Perkin reaction

Perkin reaction
Named after William Henry Perkin
Reaction type Condensation reaction
Reaction
Aromatic aldehyde
+
Aliphatic acid anhydride
+
Alkali salt of the acid
↓
Cinnamic acid derivatives
Identifiers
RSC ontology ID RXNO:0000003 checkY
 checkY(what is this?)  (verify)
Not to be confused with Perkin rearrangement.

The Perkin reaction is an organic reaction developed by English chemist William Henry Perkin that is used to make cinnamic acids. It gives an α,β-unsaturated aromatic acid or α-substituted β-aryl acrylic 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
The Perkin reaction

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

Reaction mechanism
The Perkin reaction
The Perkin reaction

Clear from the reaction mechanism, the anhydride of aliphatic acid must contain at least 2 α-H for the reaction to occur. The above mechanism is not universally accepted, as several other versions exist, including decarboxylation without acetic group transfer.[7]

Applications
  • Benzaldehyde reacts with acetic anhydride in the presence of sodium or potassium acetate to form cinnamic acid.
  • One notable application for the Perkin reaction is in the laboratory synthesis of the phytoestrogenic stilbene resveratrol (c.f. fo-ti).[8]

See also

References
  1. Perkin, W. H. (1868). "On the artificial production of coumarin and formation of its homologues". Journal of the Chemical Society. 21: 53–61. doi:10.1039/js8682100053.
  2. Perkin, W. H. (1877). "On some hydrocarbons obtained from the homologues of cinnamic acid; and on anethol and its homologues". Journal of the Chemical Society. 32: 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: 210–265. 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". Compr. Org. Synth. 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.
  8. Solladié, Guy; Pasturel-Jacopé, Yacine; Maignan, Jean (2003). "A re-investigation of resveratrol synthesis by Perkins reaction. Application to the synthesis of aryl cinnamic acids". Tetrahedron. 59 (18): 3315–3321. doi:10.1016/S0040-4020(03)00405-8. ISSN 0040-4020.
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