The
Perkin reaction is an
organic reactionOrganic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions, photochemical reactions and redox reactions. In organic synthesis,...
developed by William Henry Perkin that can be used to make
cinnamic acidCinnamic acid is a white crystalline organic acid, which is slightly soluble in water.It is obtained from oil of cinnamon, or from balsams such as storax. It is also found in shea butter and is the best indication of its environmental history and post-extraction conditions...
s i.e. α-β-unsaturated aromatic acid by the
aldol condensationAn aldol condensation is an organic reaction in which an enol or an enolate ion reacts with a carbonyl compound to form a β-hydroxyaldehyde or β-hydroxyketone, followed by a dehydration to give a conjugated enone....
of aromatic aldehydes and acid anhydrides in the presence of an alkali salt of the acid.
Several reviews have been written.. The reaction of
phenylacetic acidPhenylacetic acid is an organic compound containing a phenyl functional group and a carboxylic acid functional group. It is a white solid with a disagreeable odor...
and
benzaldehydeBenzaldehyde is an organic compound consisting of a benzene ring with a formyl substituent. It is the simplest aromatic aldehyde and one of the most industrially useful. This colorless liquid has a characteristic pleasant almond-like odor...
with
triethylamineTriethylamine is the chemical compound with the formula N3, commonly abbreviated Et3N. It is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with triethanolamine, for which TEA is also a common abbreviation....
and
acetic anhydrideAcetic anhydride, or ethanoic anhydride, is the chemical compound with the formula 2O. Commonly abbreviated Ac2O, it is the simplest isolatable acid anhydride and is a widely used reagent in organic synthesis...
to
alpha-phenylcinnamic acidα-Phenylcinnamic acid is a phenylpropanoid, or, more specifically, a derivative of cinnamic acid. It has the formula C15H12O2 and appears as an off-white crystalline solid.-Uses:...
is an example of this reaction type.
Reaction mechanism
The above mechanism is not universally accepted, as several other versions exist, including decarboxylation without acetic group transfer .
See also
- Erlenmeyer-Plöchl azlactone and amino acid synthesis
The Erlenmeyer-Plochl azlactone and amino acid synthesis, named after Friedrich Gustav Carl Emil Erlenmeyer who partly discovered the reaction, is a series of chemical reactions which transform glycine to various other amino acids via an oxazolone and an azlactone.Hippuric acid self-condenses in...
- Stobbe condensation