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]
Perkin reaction | |||||||||||
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Named after | William Henry Perkin | ||||||||||
Reaction type | Condensation reaction | ||||||||||
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RSC ontology ID | RXNO:0000003 | ||||||||||
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Reaction mechanism
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
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