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Reimer-Tiemann reaction

 

 
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Reimer-Tiemann reaction
 
 
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The Reimer-Tiemann 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....
 used for the ortho-formylation
Formylation reaction

A formylation reaction in organic chemistry is the catch-all name for any organic reaction in which an organic compound is functionalized with a formyl group ....
 of phenol
Phenol

Phenol, also known as carbolic acid, is a toxic, white crystalline solid with a sweet tarry odor, commonly referred to as a "hospital smell"....
s. The reaction was discovered by Karl Ludwig Reimer and Ferdinand Tiemann
Ferdinand Tiemann

Johann Karl Wilhelm Ferdinand Tiemann was a German chemist and together with Reimer discoverer of the Reimer-Tiemann reaction.Beginning in 1866, Tiemann studied pharmacy at the TU Braunschweig where he graduated in 1869....
. In the simplest case, the product is salicylaldehyde
Salicylaldehyde

Salicylaldehyde, or 2-hydroxybenzaldehyde, is the chemical compound with the formula C6H4CHO-2-OH. This colourless oily liquid has a bitter almond odor at higher concentration and a characteristic buckwheat aroma at lower concentration....
:


Reaction mechanism
Chloroform
Chloroform

Chloroform, also known as trichloromethane and methyl trichloride, is a chemical compound with chemical formula CarbonHydrogenChlorine3....
 (1) reacts with strong base to form the chloroform carbanion (2), which will quickly alpha-eliminate to give dichlorocarbene
Dichlorocarbene

Dichlorocarbene is a carbene commonly encountered in organic chemistry. This reactive intermediate with chemical formula CCl2 is easily available by reaction of chloroform and a base such as potassium t-butoxide or sodium hydroxide dissolved in water....
 (3).






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Encyclopedia


The Reimer-Tiemann 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....
 used for the ortho-formylation
Formylation reaction

A formylation reaction in organic chemistry is the catch-all name for any organic reaction in which an organic compound is functionalized with a formyl group ....
 of phenol
Phenol

Phenol, also known as carbolic acid, is a toxic, white crystalline solid with a sweet tarry odor, commonly referred to as a "hospital smell"....
s. The reaction was discovered by Karl Ludwig Reimer and Ferdinand Tiemann
Ferdinand Tiemann

Johann Karl Wilhelm Ferdinand Tiemann was a German chemist and together with Reimer discoverer of the Reimer-Tiemann reaction.Beginning in 1866, Tiemann studied pharmacy at the TU Braunschweig where he graduated in 1869....
. In the simplest case, the product is salicylaldehyde
Salicylaldehyde

Salicylaldehyde, or 2-hydroxybenzaldehyde, is the chemical compound with the formula C6H4CHO-2-OH. This colourless oily liquid has a bitter almond odor at higher concentration and a characteristic buckwheat aroma at lower concentration....
:

Reimer Tiemann Reaction Scheme

Reaction mechanism


Chloroform
Chloroform

Chloroform, also known as trichloromethane and methyl trichloride, is a chemical compound with chemical formula CarbonHydrogenChlorine3....
 (1) reacts with strong base to form the chloroform carbanion (2), which will quickly alpha-eliminate to give dichlorocarbene
Dichlorocarbene

Dichlorocarbene is a carbene commonly encountered in organic chemistry. This reactive intermediate with chemical formula CCl2 is easily available by reaction of chloroform and a base such as potassium t-butoxide or sodium hydroxide dissolved in water....
 (3). Dichlorocarbene will react in the ortho- and para- position of the phenate (5) to give the dichloromethyl substituted phenol (7). After basic hydrolysis, the desired product (9) is formed.

Reimer Tiemann Reaction Mechanism

See also

  • Duff reaction
    Duff reaction

    The Duff reaction or hexamine aromatic formylation is a formylation reaction used in organic chemistry for the synthesis of benzaldehydes with hexamine as the formyl carbon source ....
  • Gattermann aldehyde synthesis


Further reading