An efficient Perkin synthesis of 13 C-labelled cinnamic acids from acetic acid as the source of the rare isotope

J Labelled Comp Radiopharm. 2019 Jun 15;62(7):298-300. doi: 10.1002/jlcr.3753.

Abstract
in English, German

A variation of the Perkin reaction using a nonenolizable anhydride as the condensation agent allows for the effective conversion of valuable carboxylic acids to the corresponding cinnamates.

This practitioner protocol describes an efficient Perkin synthesis of 1-13 C-p-alkylcinnamic acids from 1-13 C-acetic acid and the benzaldehyde with caesium carbonate and pivalic anhydride as reagents. Our new method employing the nonenolizable pivalic anhydride as the condensation agent avoids the minimum threefold excess of identically labelled carboxylate moieties (in both acid and anhydride) required in a conventional Perkin synthesis to prevent isotope dilution. More generally, this variation of the Perkin synthesis broadens the scope of that classic reaction to valuable carboxylic acid components.

Keywords: Perkin reaction; cinnamic acids; isotope labelling; synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetic Acid / chemistry*
  • Carbon Isotopes / chemistry*
  • Chemistry Techniques, Synthetic
  • Cinnamates / chemical synthesis*
  • Cinnamates / chemistry*
  • Isotope Labeling
  • Radiochemistry

Substances

  • Carbon Isotopes
  • Cinnamates
  • cinnamic acid
  • Carbon-13
  • Acetic Acid