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]

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

Reaction mechanism

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

See also

References

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  5. House, H. O. (1972) Modern Synthetic Reactions, W. A. Benjamin, Menlo Park, California, 2nd ed, pp. 660–663
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  7. Bansal, Raj K. (1998) Organic Reaction Mechanisms, Tata McGraw Hill, 3rd Edition , pp. 199–201, ISBN 9780470858585 doi:10.1002/0470858583.