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Chemistry LibreTexts

Perkin Reaction

  • Page ID
    66864
  • 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. The alkali salt acts as a base catalyst, and other bases can be used instead.

    The Perkin reaction

    Several reviews have been written.

    Reaction mechanism

    The Perkin reaction

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

    Applications

    • One notable application for the Perkin reaction is in the laboratory synthesis of the phytoestrogenic stilbene resveratrol (c.f. Fo-ti).