Perkin reaction

Also known as: Perkin condensation

Schematic of the Perkin reaction. Reagents: aromatic aldehyde, anhydride, Sodium acetate (NaOAc), base, acid work-up. Product: alpha-beta-unsaturated carboxylic acid.

The Perkin reaction is an organic reaction used to convert an aromatic aldehyde and an anhydride to an α,β-unsaturated carboxylic acid using sodium acetate, a base, and an acid work-up. The regiochemistry of the reaction, the relative position of the carboxylic acid and aromatic ring in the final product, can be either E or Z. The mechanism goes through numerous steps including several additions and eliminations.[1]


Mechanism of the Perkin reaction.


Perkin, W. H. J. Chem. Soc. 1868, 21, 181