Revised mechanism and improved methodology for the Perkin condensation. Resuscitation of the mechanism involving benzal acetate and the improbability of the enolate of acetic anhydride

Article abstract of DOI:10.1016/j.tetlet.2006.01.114

The Perkin condensation most likely occurs via the initial formation of a gem-diacetate from the aromatic aldehyde and acetic anhydride reactants. The key reactive nucleophile appears to be the enolate of the gem-diacetate rather than of acetic anhydride. The diacetate from PhCHO may be converted to cinnamic acid under a variety of (relatively) mild basic conditions.