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Friedel-Crafts reaction
 
 
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The Friedel-Crafts reactions are a set of reactions
Organic reaction

Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions and organic redox reaction....
 developed by Charles Friedel
Charles Friedel

Charles Friedel was a France chemist and Mineralogy. A native of Strasbourg, France, he was professor of chemistry at the University of Paris....
 and James Crafts
James Crafts

James Mason Crafts was an United States chemist, best known for developing the Friedel-Crafts alkylation and acylation reactions with Charles Friedel in 1876....
 in 1877. There are two main types of Friedel-Crafts reactions: alkylation
Alkylation

Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion or a carbene ....
 reactions and acylation
Acylation

In chemistry, acylation is the process of adding an acyl group to a compound. The compound providing the acyl group is called the acylating agent....
 reactions. This reaction type is part of electrophilic aromatic substitution
Electrophilic aromatic substitution

Electrophilic aromatic substitution or EAS is an organic reaction in which an atom, usually hydrogen, appended to an aromatic ring is replaced by an electrophile....
. The general reaction scheme is shown below.

Several reviews have been written.

del-Crafts alkylation involves the alkylation of an aromatic ring and an alkyl halide using a strong Lewis acid
Lewis acid

A Lewis acid is a chemical compound, A, that can accept a pair of electrons from a Lewis base, B, that acts as an electron-pair donor, forming an adduct, AB.Gilbert N....
 catalyst.






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Encyclopedia


The Friedel-Crafts reactions are a set of reactions
Organic reaction

Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions and organic redox reaction....
 developed by Charles Friedel
Charles Friedel

Charles Friedel was a France chemist and Mineralogy. A native of Strasbourg, France, he was professor of chemistry at the University of Paris....
 and James Crafts
James Crafts

James Mason Crafts was an United States chemist, best known for developing the Friedel-Crafts alkylation and acylation reactions with Charles Friedel in 1876....
 in 1877. There are two main types of Friedel-Crafts reactions: alkylation
Alkylation

Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion or a carbene ....
 reactions and acylation
Acylation

In chemistry, acylation is the process of adding an acyl group to a compound. The compound providing the acyl group is called the acylating agent....
 reactions. This reaction type is part of electrophilic aromatic substitution
Electrophilic aromatic substitution

Electrophilic aromatic substitution or EAS is an organic reaction in which an atom, usually hydrogen, appended to an aromatic ring is replaced by an electrophile....
. The general reaction scheme is shown below.

Several reviews have been written.

Friedel-Crafts alkylation

Friedel-Crafts alkylation involves the alkylation of an aromatic ring and an alkyl halide using a strong Lewis acid
Lewis acid

A Lewis acid is a chemical compound, A, that can accept a pair of electrons from a Lewis base, B, that acts as an electron-pair donor, forming an adduct, AB.Gilbert N....
 catalyst. With anhydrous ferric chloride as a catalyst, the alkyl group attaches at the former site of the chloride ion. The general mechanism is shown below.

This reaction has one big disadvantage, namely that the product is more nucleophilic
Nucleophile

In chemistry, a nucleophile is a reagent that forms a chemical bond to its reaction partner by donating both bonding electrons. Because nucleophiles donate electrons, they are by definition Lewis bases ....
 than the reactant due to the electron donating alkyl-chain. Therefore, another hydrogen is substituted with an alkyl-chain, which leads to overalkylation of the molecule. Also, if the chlorine is not on a tertiary carbon, carbocation
Carbocation

A carbocation is an ion with a positively-charged carbon atom. The charged carbon atom in a carbocation is a "sextet", i.e. it has only six electrons in its outer Electron shell#Valence shell instead of the eight valence electrons that ensures maximum stability ....
 rearrangement reaction
Rearrangement reaction

A rearrangement reaction is a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule ....
 will occur. This is due to the relative stability of the tertiary carbocation
Carbocation

A carbocation is an ion with a positively-charged carbon atom. The charged carbon atom in a carbocation is a "sextet", i.e. it has only six electrons in its outer Electron shell#Valence shell instead of the eight valence electrons that ensures maximum stability ....
 over the secondary and primary carbocations.

Steric hindrance can be exploited to limit the number of alkylations, as in the t-butylation of 1,4-dimethoxybenzene.
Alkylations are not limited to alkyl halides: Friedel-Crafts reactions are possible with any carbocation
Carbocation

A carbocation is an ion with a positively-charged carbon atom. The charged carbon atom in a carbocation is a "sextet", i.e. it has only six electrons in its outer Electron shell#Valence shell instead of the eight valence electrons that ensures maximum stability ....
ic intermediate such as those derived from alkene
Alkene

In organic chemistry, an alkene, olefin, or olefine is an Saturation chemical compound containing at least one carbon-to-carbon double bond....
s and a protic acid, lewis acid
Lewis acid

A Lewis acid is a chemical compound, A, that can accept a pair of electrons from a Lewis base, B, that acts as an electron-pair donor, forming an adduct, AB.Gilbert N....
, enone
Enone

An enone is an saturation chemical compound or functional group consisting of a conjugated system of an alkene and a ketone. The simplest enone is methyl vinyl ketone or CH2=CHCOCH3....
s, and epoxide
Epoxide

An epoxide is a cyclic ether with only three ring atoms. This ring approximately is an equilateral triangle which makes it highly ring strain....
s. In one study the electrophile is a bromonium ion derived from an alkene and NBS
N-Bromosuccinimide

N-Bromosuccinimide or NBS is a chemical reagent which is used in radical substitution and electrophilic addition chemical reaction in organic chemistry....
:

In this reaction samarium(III) triflate is believed to activate the NBS halogen donor in halonium ion formation.


Friedel-Crafts dealkylation

Friedel-Crafts alkylation is a reversible reaction
Reversible reaction

A reversible reaction is a chemical reaction that results in an chemical equilibrium mixture of reactants and Product . For a reaction involving two reactants and two products this can be expressed symbolically asA and B can react to form C and D or, in the reverse reaction, C and D can react to form A and B....
. In a reversed Friedel-Crafts reaction or Friedel-Crafts dealkylation, alkyl groups can be removed in the presence of protons and a Lewis acid
Lewis acid

A Lewis acid is a chemical compound, A, that can accept a pair of electrons from a Lewis base, B, that acts as an electron-pair donor, forming an adduct, AB.Gilbert N....
.

For example, in a multiple addition of ethyl bromide
Bromoethane

Bromoethane, also known as ethyl bromide is a chemical compound of the haloalkanes group. It is abbreviated by chemists as EtBr. This volatile compound has an ether-like odour....
 to benzene
Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
, ortho and para substitution
Arene substitution patterns

Arene substitution patterns are part of organic chemistry IUPAC nomenclature and pinpoint the position of substituents other than hydrogen in relation to each other on an aromatic hydrocarbon....
 is expected after the first monosubstitution step because an alkyl group is an activating group
Activating group

In organic chemistry, a functional group is called an activating group if a benzene molecule to which it is attached more readily participates in electrophilic substitution reactions....
. However, the actual reaction product is 1,3,5-triethylbenzene with all alkyl groups as a meta substituent. Thermodynamic reaction control
Thermodynamic reaction control

Thermodynamic reaction control or kinetic reaction control in a chemical reaction can decide the composition in a reaction product mixture when competing pathways lead to different products and the reaction conditions influence the selectivity....
 makes sure that thermodynamically favored meta substitution with steric hindrance minimized takes prevalence over less favorable ortho and para substitution by chemical equilibration
Chemical equilibrium

In a chemical process, chemical equilibrium is the state in which the Activity or concentrations of the reactants and products have no net change over time....
. The ultimate reaction product is thus the result of a series of alkylations and dealkylations.


Friedel-Crafts acylation


Friedel-Crafts acylation is the acylation
Acylation

In chemistry, acylation is the process of adding an acyl group to a compound. The compound providing the acyl group is called the acylating agent....
 of aromatic rings with an acyl chloride
Acyl chloride

In organic chemistry, an acyl chloride is an organic compound which is a reactive derivative of a carboxylic acid. As part of its molecular structure, an acyl chloride has the reactive functional group -Carbonyl-Chlorine and has the general formula RCOCl, where R is an organic radical group....
 using a strong Lewis acid
Lewis acid

A Lewis acid is a chemical compound, A, that can accept a pair of electrons from a Lewis base, B, that acts as an electron-pair donor, forming an adduct, AB.Gilbert N....
 catalyst. Friedel-Crafts acylation is also possible with acid anhydrides. Reaction conditions are similar to the Friedel-Crafts alkylation mentioned above. This reaction has several advantages over the alkylation reaction. Due to the electron-withdrawing effect of the carbonyl
Carbonyl

In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double bond to an oxygen atom : C=O.The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex ; in this situation, carbon is triple-bonded to oxygen : C=O....
 group, the ketone
Ketone

In organic chemistry, a ketone is a type of organic compound which contains a carbonyl group bonded to two other carbon atoms in the form:Neither of the substituents R1 and R2 may be equal to hydrogen ....
 product is always less reactive than the original molecule, so multiple acylations do not occur. Also, there are no carbocation
Carbocation

A carbocation is an ion with a positively-charged carbon atom. The charged carbon atom in a carbocation is a "sextet", i.e. it has only six electrons in its outer Electron shell#Valence shell instead of the eight valence electrons that ensures maximum stability ....
 rearrangements, as the carbonium ion is stabilized by a resonance structure in which the positive charge is on the oxygen.



The viability of the Friedel-Crafts acylation depends on the stability of the acyl chloride reagent. Formyl chloride, for example, is too unstable to be isolated. Thus, synthesis of benzaldehyde
Benzaldehyde

Benzaldehyde is a chemical compound consisting of a benzene ring with an aldehyde substituent. It is the simplest representative of the aromatic aldehydes and one of the most industrially used members of this family of compounds....
 via the Friedel-Crafts pathway requires that formyl chloride be synthesized in situ. This is accomplished via the Gattermann-Koch reaction
Gattermann-Koch reaction

The Gattermann-Koch reaction, named for the German chemists Ludwig Gattermann and Julius Arnold Koch, in organic chemistry refers to a Friedel-Crafts acylation reaction in which carbon monoxide and hydrochloric acid are used in-situ with Friedel-Crafts catalyst, namely AlCl3 to produce a benzaldehyde-derivative from a benzene-deriv...
, accomplished by reacting benzene
Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
 with carbon monoxide
Carbon monoxide

Carbon monoxide, with the chemical formula CO, is a colorless and odorless, tasteless, yet highly toxic gas. Its molecules consist of one carbon atom covalent bond to one oxygen atom....
 and hydrogen chloride
Hydrogen chloride

The Chemical compound hydrogen chloride has the chemical formula HydrogenChlorine. At room temperature, it is a colorless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric humidity....
 under high pressure, catalyzed by a mixture of aluminium chloride
Aluminium chloride

Aluminium chloride is a chemical compound of aluminium and chlorine. The solid has a low melting and boiling point, and is Covalent bond. It sublimation at 178 ?Celsius....
 and cuprous chloride.

Reaction mechanism


In a simple mechanistic view, the first step consists of dissociation of a chlorine atom to form an acyl
Acyl

An acyl group is a functional group derived by the removal of one or more hydroxyl groups from an oxoacid.. In organic chemistry, the acyl group is usually derived from a carboxylic acid of the form RCarbon Oxygen hydroxyl....
 cation:

This is followed by nucleophilic attack of the arene toward the acyl group:

Finally, a chlorine atom reacts to form HCl, and the AlCl3 catalyst is regenerated:


Friedel-Crafts hydroxyalkylation

Arenes react with certain aldehyde
Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
s and ketone
Ketone

In organic chemistry, a ketone is a type of organic compound which contains a carbonyl group bonded to two other carbon atoms in the form:Neither of the substituents R1 and R2 may be equal to hydrogen ....
s to the hydroxyalkylated product for example in the reaction of the mesityl derivative of glyoxal
Glyoxal

Glyoxal is an organic compound with the formula OCHCHO. This yellow colored liquid is the smallest dialdehyde ....
 with benzene to form a benzoin
Benzoin

Benzoin or 2-Hydroxy-2-phenylacetophenone or 2-Hydroxy-1,2-Diphenylethanone or desyl alcohol or bitter almond oil camphor is an organic compound consisting of an ethylene bridge flanked by phenyl groups and with a hydroxyl and a ketone functional group....
 with an alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
 rather than a carbonyl
Carbonyl

In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double bond to an oxygen atom : C=O.The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex ; in this situation, carbon is triple-bonded to oxygen : C=O....
 group:


Scope & variations

This reaction is related to several classic named reactions:
  • The acylated reaction product can be converted into the alkylated product via a Clemmensen reduction
    Clemmensen reduction

    The Clemmensen reduction is a chemical reaction described as a redox of ketones to alkanes using zinc amalgam and hydrochloric acid. This reaction is named after Erik Christian Clemmensen, a Danish chemist....
    .
  • The Gattermann-Koch reaction
    Gattermann-Koch reaction

    The Gattermann-Koch reaction, named for the German chemists Ludwig Gattermann and Julius Arnold Koch, in organic chemistry refers to a Friedel-Crafts acylation reaction in which carbon monoxide and hydrochloric acid are used in-situ with Friedel-Crafts catalyst, namely AlCl3 to produce a benzaldehyde-derivative from a benzene-deriv...
     can be used to synthesize benzaldehyde from benzene.
  • The Gatterman reaction describes arene reactions with hydrocyanic acid
  • The Houben-Hoesch reaction describes arene reactions with nitriles
  • A reaction modification with an aromatic phenyl ester as a reactant is called the Fries rearrangement
    Fries rearrangement

    The Fries rearrangement, named for the German chemist Karl Theophil Fries, is a rearrangement reaction of a phenyl ester to a hydroxy aryl ketone by catalysis of lewis acids....
    .
  • In the Scholl reaction
    Scholl reaction

    The Scholl reaction is a coupling reaction between two arene compounds with the aid of a Lewis acid and a protic acid.The protic acid is often an impurity in the Lewis Acid and also formed in the course of a Scholl reaction....
     two arenes couple directly (sometimes called Friedel-Crafts arylation).
  • In the Zincke-Suhl reaction
    Zincke-Suhl reaction

    The Zincke-Suhl reaction is a special case of a Friedel-Crafts alkylation and was first described by Theodor Zincke and Suhl.The classic example of this reaction is the conversion of p-cresol to a cyclohexadienone ....
     p-cresol is alkylated to a cyclohexadienone with tetrachloromethane
  • In the Blanc chloromethylation
    Blanc chloromethylation

    The Blanc chloromethylation is the chemical reaction of aromatic rings with formaldehyde and hydrogen chloride catalyzed by zinc chloride to form chloromethyl arenes....
     a chloromethyl group is added to an arene with formaldehyde, hydrochloric acid and zinc chloride.
  • The Bogert-Cook Synthesis (1933) involves the dehydration
    Dehydration

    Dehydration is the removal of water from an object. In Physiology terms, it entails a relative deficiency of water molecules in relation to other dissolved solutes....
     and isomerization of 1-ß-phenylethylcyclohexanol to the octahydro derivative of phenanthrene
    Phenanthrene

    Phenanthrene is a polycyclic aromatic hydrocarbon composed of three fused benzene rings. The name phenanthrene is a composite of phenyl and anthracene....
     
  • The Darzens-Nenitzescu Synthesis of Ketones (1910, 1936) involves the acylation of cyclohexene
    Cyclohexene

    Cyclohexene is a colorless clear liquid cycloalkene with an intense aversive characteristic sharp smell reminiscent of an oil refinery.It is not very stable upon long term storage with exposure to light and air and should be distilled before use to eliminate organic peroxide....
     with acetyl chloride
    Acetyl chloride

    Acetyl chloride is an acid chloride derived from acetic acid. It has the formula CH3COCl and it belongs to the class of organic compounds called acyl halides....
     to methylcyclohexenylketone.
  • In the related Nenitzescu reductive acylation (1936) a saturated hydrocarbon
    Hydrocarbon

    In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. With relation to chemical terminology, aromatic hydrocarbons or arenes, alkanes, alkenes and alkyne-based compounds composed entirely of carbon or hydrogen are referred to as "pure" hydrocarbons, whereas other hydrocarbons with bonded com...
     is added making it a reductive acylation to methylcyclohexylketone
  • In a green chemistry
    Green chemistry

    Green chemistry, also called sustainable chemistry, is a chemical philosophy encouraging the design of products and processes that reduce or eliminate the use and generation of hazardous substances....
     variation aluminium chloride
    Aluminium chloride

    Aluminium chloride is a chemical compound of aluminium and chlorine. The solid has a low melting and boiling point, and is Covalent bond. It sublimation at 178 ?Celsius....
     is replaced by graphite
    Graphite

    The mineral graphite is one of the allotropes of carbon. It was named by Abraham Gottlob Werner in 1789 from the Greek language ??afe?? : "to draw/write", for its use in pencils, where it is commonly called lead, as distinguished from the actual metallic element lead....
     in an alkylation of p-xylene
    P-Xylene

    p-Xylene is an aromatic hydrocarbon, based on benzene with two methyl substituents. The ?p? stands for para, identifying the location of the methyl groups as across from one another....
     with 2-bromobutane. This variation will not work with primary halides from which less carbocation involvement is inferred.

Dyes

Friedel-Crafts reactions have been used in the synthesis of several triarylmethane
Triphenylmethane

Triphenylmethane, or triphenyl methane, is the hydrocarbon with the chemical formula 3CH. This colorless solid is soluble in nonpolar organic solvents, but not water....
 and xanthene
Xanthene

Xanthene is a yellow organic compound heterocyclic compound. Its chemical formula is 1310. It is soluble in diethyl ether....
 dye
Dye

A dye can generally be described as a colored substance that has an Chemical affinity to the Wiktionary:substrate to which it is being applied....
s . Examples are the synthesis of thymolphthalein
Thymolphthalein

Thymolphthalein is an acid-base PH indicator. Its transition range is at approximately pH 9.3-10.5. Below this pH, it is colorless; above this pH, it is blue....
 (a pH indicator) from two equivalents of thymol
Thymol

Thymol also known as isopropylmethylphenol, is a monoterpene phenols derivative of cymene, C10H14OH, isomeric with carvacrol, found in oil of thyme, and Liquid-liquid extraction as a white crystalline substance of a pleasant aromatic odor and strong antiseptic properties....
 and phthalic anhydride
Phthalic anhydride

Phthalic anhydride is the organic compound with the chemical formula C6H42O. This anhydride of phthalic acid, a colourless solid, is an important industrial chemical, especially for the large-scale production of plasticizers for plastics....
:

A reaction of phthalic anhydride with resorcinol
Resorcinol

Resorcinol is a chemical compound from the dihydroxy phenols. It is the 1,3-isomer of benzenediol, and is also known with a variety of other names, including: m-dihydroxybenzene, 1,3-benzenediol, 1,3-dihydroxybenzene, 3-hydroxyphenol, m-hydroquinone, m-benzenediol, and 3-hydroxycyclohexadien-1-one....
 in the presence of zinc chloride
Zinc chloride

Zinc chloride is the name of chemical compound with the chemical formula zincchlorine2 and its hydrates. Zinc chlorides, of which nine crystalline forms are known, are colorless or white and highly soluble in water....
 gives the fluorophore Fluorescein
Fluorescein

Fluorescein is a fluorophore commonly used in microscopy, in a type of dye laser as the gain medium, in forensics and serology to detect latent blood stains, and in dye tracing....
. Replacing resorcinol by N,N-diethylaminophenol in this reaction gives rhodamine B
Rhodamine B

Rhodamine B is used in biology as a staining fluorescent dye, sometimes in combination with auramine O, as the auramine-rhodamine stain to demonstrate acid-fast organisms, notably Mycobacterium....
:


Haworth reactions

The Haworth reaction is a classic method for the synthesis of tetralone.. In it benzene
Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
 is reacted with succinic anhydride
Succinic anhydride

Succinic anhydride, also called dihydro-2,5-furandione, is an organic compound with the molecular formula C4H4O3. It is the acid anhydride of succinic acid....
, the intermediate product is reduced and a second FC acylation takes place with addition of acid.

In a related reaction, phenanthrene
Phenanthrene

Phenanthrene is a polycyclic aromatic hydrocarbon composed of three fused benzene rings. The name phenanthrene is a composite of phenyl and anthracene....
 is synthesized from naphthalene
Naphthalene

Naphthalene, also known as naphthalin, naphthaline, tar camphor, white tar, albocarbon, or antimite and not to be confused with naphtha, is a crystalline, Aromaticity, white, solid hydrocarbon with formula Carbon10hydrogen8 and the structure of two fused benzene rings....
 and succinic anhydride
Succinic anhydride

Succinic anhydride, also called dihydro-2,5-furandione, is an organic compound with the molecular formula C4H4O3. It is the acid anhydride of succinic acid....
 in a series of steps.


Friedel-Crafts test for aromatic hydrocarbons

Reaction of chloroform
Chloroform

Chloroform, also known as trichloromethane and methyl trichloride, is a chemical compound with chemical formula CarbonHydrogenChlorine3....
 with aromatic compounds using an aluminium chloride
Aluminium chloride

Aluminium chloride is a chemical compound of aluminium and chlorine. The solid has a low melting and boiling point, and is Covalent bond. It sublimation at 178 ?Celsius....
 catalyst gives triarylmethanes, which are often brightly colored, as is the case in triarylmethane dyes. This is a bench test for aromatic compounds.

FC (Friedlel-Crafts) reactions in Org. Synth.

Friedel-Crafts reactions appear in Organic Syntheses
Organic Syntheses

Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds....
:
  • Alkylations:
    • Diphenylacetone, Organic Syntheses, Coll. Vol. 3, p.343 (1955); Vol. 29, p.38 (1949) .
    • Reaction of p-xylene
      P-Xylene

      p-Xylene is an aromatic hydrocarbon, based on benzene with two methyl substituents. The ?p? stands for para, identifying the location of the methyl groups as across from one another....
       with chloromethane
      Chloromethane

      Chloromethane, also called Methyl chloride, R-40 or HCC 40, is a chemical compound of the group of organic compounds called haloalkanes. It was once widely used as a refrigeration....
       to durene
      Durene

      Durene, or 1,2,4,5-tetramethylbenzene, is an aromatic hydrocarbon used as a solvent. It is also an intermediate in the manufacture of pyromellitic acid, which is used for manufacturing curing agents, adhesives and coating materials....
       Organic Syntheses, Coll. Vol. 2, p.248 (1943); Vol. 10, p.32 (1930).
    • Synthesis of benzophenone
      Benzophenone

      Benzophenone is the organic compound with the formula 2Coxygen, generally abbreviated phenyl2CO. Benzophenone is a widely used building block in organic chemistry, being the parent diarylketone....
       from benzene
      Benzene

      Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
       and tetrachloromethane Organic Syntheses, Coll. Vol. 1, p.95 (1941); Vol. 8, p.26 (1928).
  • Acylations:
    • Dibenzoylethylene Organic Syntheses, Coll. Vol. 3, p.248 (1955); Vol. 20, p.29 (1940) .
    • reaction of acenaphthene
      Acenaphthene

      Acenaphthene is a polycyclic aromatic hydrocarbon consisting of naphthalene with an ethylene bridge connecting positions 1 and 8. An alternative name, 1,2-dihydroacenaphthylene, emphasizes that it is a hydrogenated form of acenaphthylene....
       plus succinic acid
      Succinic acid

      Succinic acid is a dicarboxylic acid. Succinate plays a biochemical role in the citric acid cycle....
       Organic Syntheses, Coll. Vol. 3, p.6 (1955); Vol. 20, p.1 (1940).
    • Desoxybenzoin Organic Syntheses, Coll. Vol. 2, p.156 (1943); Vol. 12, p.16 (1932).
    • Acylation of a phenanthrene
      Phenanthrene

      Phenanthrene is a polycyclic aromatic hydrocarbon composed of three fused benzene rings. The name phenanthrene is a composite of phenyl and anthracene....
       compound Organic Syntheses, Vol. 80, p.227
    • Reaction of bromobenzene
      Bromobenzene

      Bromobenzenes are a group of halocarbons formed in a substitution reaction between bromine and benzene with a hydrogen bromide by-product. The name strictly refers to monobromobenzene, a benzene with a single bromine; however it can be used to refer to a benzene containing any number of bromine molecules....
       with acetic anhydride
      Acetic anhydride

      Acetic anhydride is the chemical compound with the chemical formula 2O. Commonly abbreviated Acetyl2O, it is one of the simplest acid anhydrides and is a widely used reagent in organic synthesis....
       Organic Syntheses, Coll. Vol. 1, p.109 (1941); Vol. 5, p.17 (1925).
    • beta-methylanthraquinone, Organic Syntheses, Coll. Vol. 1, p.353 (1941); Vol. 4, p.43 (1925).
    • Benzoylation of ferrocene
      Ferrocene

      Ferrocene is the organometallic compound with the formula Fe2. It is the prototypical metallocene, a type of organometallic chemistry chemistry compound consisting of two cyclopentadienyl complex rings bound on opposite sides of a central metal atom....
       Organic Syntheses, Coll. Vol. 6, p.625 (1988); Vol. 56, p.28 (1977).


See also

  • Darzens-Nenitzescu synthesis of ketones
  • Nencki reaction
  • Charles Friedel
    Charles Friedel

    Charles Friedel was a France chemist and Mineralogy. A native of Strasbourg, France, he was professor of chemistry at the University of Paris....
  • Friedel family
    Friedel family

    Four French scientists with the same Friedel family name are in direct lineage, Charles Friedel, Georges Friedel, Edmond Friedel and Jacques Friedel:...
    , a rich lineage of French scientists