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

Dominik Lenz, Benjamin Koeppe, P.M. Tolstoy, Hans-Heinrich Limbach

Research outputpeer-review

Abstract

This practitioner protocol describes an efficient Perkin synthesis of 1‐13C‐p‐alkylcinnamic acids from 1‐13C‐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.
Original languageEnglish
Pages (from-to)298-300
Number of pages3
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume62
Issue number7
DOIs
Publication statusPublished - 15 Jun 2019

Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Radiology Nuclear Medicine and imaging
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

Cite this

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abstract = "This practitioner protocol describes an efficient Perkin synthesis of 1‐13C‐p‐alkylcinnamic acids from 1‐13C‐acetic acid and the benzaldehyde with caesiumcarbonate and pivalic anhydride as reagents. Our new method employing thenonenolizable 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.",
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An efficient Perkin synthesis of 13C‐labelled cinnamic acids from acetic acid as the source of the rare isotope. / Lenz, Dominik; Koeppe, Benjamin; Tolstoy, P.M.; Limbach, Hans-Heinrich.

In: Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 62, No. 7, 15.06.2019, p. 298-300.

Research outputpeer-review

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