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Tishchenko reaction

 
Tishchenko Reaction

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Tishchenko reaction



 
 
The Tishchenko reaction is a chemical reaction
Chemical reaction

A chemical reaction is a process that always results in the interconversion of chemical substances. The substance or substances initially involved in a chemical reaction are called reactants....
 that involves disproportionation
Disproportionation

Disproportionation or dismutation is used to describe two particular types of chemical reaction:* A chemical reaction of the type: 2A ? A' + A" where A, A' and A" are different chemical species....
 of an 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....
 lacking a hydrogen atom in the alpha position in the presence of an alkoxide
Alkoxide

An alkoxide is the conjugate base of an alcohol and therefore consists of an organic group bonded to a negatively charged oxygen atom. They can be written as RO–, where R is the organic substituent....
. The reaction product is an ester
Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
. Catalysts are aluminium alkoxides or sodium alkoxides. 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....
 reacts with sodium benzyloxide (generated from sodium
Sodium

Sodium is an element which has the symbol Na , atomic number 11, atomic mass 23 amu , and a common oxidation number +1. Sodium is a soft, silvery white, highly reactive element and is a member of the alkali metals within "group 1" ....
 and benzyl alcohol
Benzyl alcohol

Benzyl alcohol is an organic compound with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn", thus benzyl alcohol is denoted as BnOH....
) to benzyl benzoate
Benzyl benzoate

Benzyl benzoate is the ester of benzyl alcohol and benzoic acid, with the formula C6H5CH2O2CC6H5....
.

Paraformaldehyde
Formaldehyde

Formaldehyde is a chemical compound with the chemical formula H2CO. It is the simplest aldehyde. Formaldehyde exists in several forms aside from H2CO: the cyclic trimer trioxane and the polymer Polyoxymethylene....
 reacts with boric acid
Boric acid

Boric acid, also called boracic acid or orthoboric acid or Acidum Boricum, is a weak acid often used as an antiseptic, insecticide, flame retardant, in nuclear power plants to control the fission rate of uranium, and as a precursor of other chemical compounds....
 to methyl formate
Methyl formate

Methyl formate, also called methyl methanoate, is the methyl ester of formic acid. It is a clear liquid with an ethereal odor, high vapor pressure and low surface tension....
.






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Encyclopedia


The Tishchenko reaction is a chemical reaction
Chemical reaction

A chemical reaction is a process that always results in the interconversion of chemical substances. The substance or substances initially involved in a chemical reaction are called reactants....
 that involves disproportionation
Disproportionation

Disproportionation or dismutation is used to describe two particular types of chemical reaction:* A chemical reaction of the type: 2A ? A' + A" where A, A' and A" are different chemical species....
 of an 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....
 lacking a hydrogen atom in the alpha position in the presence of an alkoxide
Alkoxide

An alkoxide is the conjugate base of an alcohol and therefore consists of an organic group bonded to a negatively charged oxygen atom. They can be written as RO–, where R is the organic substituent....
. The reaction product is an ester
Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
. Catalysts are aluminium alkoxides or sodium alkoxides. 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....
 reacts with sodium benzyloxide (generated from sodium
Sodium

Sodium is an element which has the symbol Na , atomic number 11, atomic mass 23 amu , and a common oxidation number +1. Sodium is a soft, silvery white, highly reactive element and is a member of the alkali metals within "group 1" ....
 and benzyl alcohol
Benzyl alcohol

Benzyl alcohol is an organic compound with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn", thus benzyl alcohol is denoted as BnOH....
) to benzyl benzoate
Benzyl benzoate

Benzyl benzoate is the ester of benzyl alcohol and benzoic acid, with the formula C6H5CH2O2CC6H5....
.

Tishchenko Reaction
Paraformaldehyde
Formaldehyde

Formaldehyde is a chemical compound with the chemical formula H2CO. It is the simplest aldehyde. Formaldehyde exists in several forms aside from H2CO: the cyclic trimer trioxane and the polymer Polyoxymethylene....
 reacts with boric acid
Boric acid

Boric acid, also called boracic acid or orthoboric acid or Acidum Boricum, is a weak acid often used as an antiseptic, insecticide, flame retardant, in nuclear power plants to control the fission rate of uranium, and as a precursor of other chemical compounds....
 to methyl formate
Methyl formate

Methyl formate, also called methyl methanoate, is the methyl ester of formic acid. It is a clear liquid with an ethereal odor, high vapor pressure and low surface tension....
. The key step in the reaction mechanism
Reaction mechanism

In chemistry, a reaction mechanism is the step by step sequence of elementary reactions by which overall chemical change occurs .Although only the net chemical change is directly observation for most chemical reactions, experiments can often be designed that suggest the possible sequence of steps in a reaction mechanism....
 for this reaction is a 1,3-hydride shift in the hemiacetal
Hemiacetal

Hemiacetals and hemiketals are compounds of the general formula R1R'1COR2, where R2 is not hydrogen....
 intermediate formed from two successive nucleophilic addition
Nucleophilic addition

In organic chemistry, a nucleophilic addition reaction is an addition reaction where in a chemical compound a p bond is removed by the creation of two new covalent bonds by the addition of a nucleophile ....
 reactions, the first one from the catalyst. The hydride shift regenerates the alkoxide catalyst.

Tishchenko Reaction Mechanism
In the related Cannizzaro reaction
Cannizzaro reaction

The Cannizzaro reaction, named after its discoverer Stanislao Cannizzaro, is a chemical reaction that involves the base -induced disproportionation of an aldehyde lacking a hydrogen atom in the alpha position....
 the base is sodium hydroxide
Sodium hydroxide

Sodium hydroxide , also known as lye, caustic soda and sodium hydrate, is a caustic metallic Base . Sodium hydroxide forms a strong alkaline solution when dissolved in a solvent such as water, however, only the hydroxide ion is basic....
 and then the oxidation product is a carboxylic acid
Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
 and the reduction product is 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....
.

Related reactions

  • Aldol-Tishchenko reaction
    Aldol-Tishchenko reaction

    The Aldol-Tishchenko reaction is a tandem reaction involving an Aldol reaction and a Tishchenko reaction. In organic synthesis it is a method to convert aldehydes and ketones into 1,3-hydroxyl compounds....
  • Baylis-Hillman reaction
    Baylis-Hillman reaction

    The Baylis-Hillman reaction is an organic reaction of an aldehyde and an a,?-saturation electron-withdrawing group catalyzed by DABCO to give an allyl alcohol ....
  • Cannizzaro reaction
    Cannizzaro reaction

    The Cannizzaro reaction, named after its discoverer Stanislao Cannizzaro, is a chemical reaction that involves the base -induced disproportionation of an aldehyde lacking a hydrogen atom in the alpha position....
  • Meerwein-Ponndorf-Verley Reduction
    Meerwein-Ponndorf-Verley reduction

    The Meerwein-Ponndorf-Verley Reduction in organic chemistry is the organic reduction of ketones to secondary alcohols with aluminumisopropylate catalysis in isopropanol solution ....
  • Oppenauer Oxidation
    Oppenauer oxidation

    Oppenauer oxidation, named after Rupert Viktor Oppenauer , is a gentle method for organic oxidation secondary alcohols to ketones.The reaction is the opposite of Meerwein-Ponndorf-Verley reduction....