Perkin reaction

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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 YesY
 YesY(what is this?)  (verify)

The Perkin reaction is an organic reaction developed by William Henry Perkin that is used to make cinnamic acids. It gives an α,β-unsaturated aromatic acid by the aldol condensation of an aromatic aldehyde and an acid anhydride, in the presence of an alkali salt of the acid.[1][2] The alkali salt acts as a base catalyst, and other bases can be used instead.[3]

The Perkin reaction

Several reviews have been written.[4][5][6]

Reaction mechanism[edit]

The Perkin reaction

The above mechanism is not universally accepted, as several other versions exist, including decarboxylation without acetic group transfer.[7]

See also[edit]

References[edit]

  1. ^ Perkin, W. H. (1868). "VI.—On the artificial production of coumarin and formation of its homologues". J. Chem. Soc. 21: 53, 181–186. doi:10.1039/js8682100053. 
  2. ^ Perkin, W. H. (1877). "XXVIII.—On some hydrocarbons obtained from the homologues of cinnamic acid; and on anethol and its homologues". J. Chem. Soc. 31: 660–674. doi:10.1039/js8773200660. 
  3. ^ Dippy, J. F. J.; Evans, R. M. (1950). "The nature of the catalyst in the Perkin condensation". J. Org. Chem. 15 (3): 451–456. doi:10.1021/jo01149a001. 
  4. ^ Johnson, J. R. (1942). "The Perkin Reaction and Related Reactions". Org. React. 1: 210. doi:10.1002/0471264180.or001.08. ISBN 0471264180. 
  5. ^ House, H. O. (1972) Modern Synthetic Reactions, W. A. Benjamin, Menlo Park, California, 2nd ed, pp. 660–663
  6. ^ Rosen, T. (1991). "The Perkin Reaction". Comp. Org. Syn. 2: 395–408. doi:10.1016/B978-0-08-052349-1.00034-2. ISBN 978-0-08-052349-1. 
  7. ^ Bansal, Raj K. (1998) Organic Reaction Mechanisms, Tata McGraw Hill, 3rd Edition , pp. 199–201, ISBN 9780470858585 doi:10.1002/0470858583.