This reaction named after W.H. Perkin, He described the synthesis of coumarin in one-pot by heating the salt sodium salicylaldehyde in acetic anhydride.
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What is Perkin reaction (or Perkin condensation)?
The Perkin reaction (or Perkin condensation) is an condensation of aromatic aldehydes and the anhydrides of aliphatic carboxylic acids in the presence of a weak base to obtain α,β-unsaturated carboxylic acids.
the catalyst used in Perkin reaction is acetic anhydrides and base: NaOAc, KOAc, CsOAc, Et3N, pyridine, piperidine, K2CO3, aliphatic aldehydes with no α-hydrogens as well as certain α,β unsaturated aldehydes can also be used. The final product of Perkin reaction is α,β-unsaturated carboxylic acids. Synthesis of coumarins is one of the application of Perkin reaction.
Perkin Reaction Mechanism:
Perkin Reaction examples and applications:
Related reactions :
- Pechmann condensation
- Stobbe condensation
My name is Pradip Sanjay W. I’m an organic chemist originally from Maharashtra, India. I have qualified UGC NET-JRF, GATE in chemical sciences and MH-SET exam for assistant professor. I’m currently pursuing my Ph.D. in organic chemistry at the Indian Institute of Technology Hyderabad, India.