Perkin reaction

Perkin reaction
Named after William Henry Perkin
Reaction type Condensation reaction
Reaction
Aromatic aldehyde
+
Acid anhydride
+
Alkali salt of the acid
↓
Cinnamic acid derivatives
Identifiers
RSC ontology ID RXNO:0000003 Y
 Y(what is this?)  (verify)

The Perkin reaction is an organic reaction developed by William Henry Perkin that can be used to make cinnamic acids i.e. α-β-unsaturated aromatic acid by the aldol condensation of aromatic aldehydes and acid anhydrides in the presence of an alkali salt of the acid.[1][2]

Several reviews have been written.[3][4][5]. The reaction of phenylacetic acid and benzaldehyde with triethylamine and acetic anhydride to alpha-phenylcinnamic acid 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 [6].

References

  1. ^ Perkin, W. H.; J. Chem. Soc. 1868, 21, 53, 181-186.
  2. ^ Perkin, W. H.; J. Chem. Soc. 1877, 31, 660-674.
  3. ^ Johnson, J. R.; Org. React. 1942, 1, 210. (Review)
  4. ^ House, H. O. Modern Synthetic Reactions (W. A. Benjamin, Menlo Park, California, 2nd ed, 1972) pp 660-663.
  5. ^ Rosen, T.; Comp. Org. Syn. 1991, 2, 395-408. (Review)
  6. ^ Bansal, Raj K. Organic Reaction Mechanisms, Tata McGraw Hill, 3rd Edition , 1998, pp. 199-201.

See also