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Acetoacetic Ester Condensation

(Claisen-Geuther Ester Condensation)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr002

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Acetoacetic Ester Condensation. Comprehensive Organic Name Reactions and Reagents. 2:5–8.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

Acetoacetic ester condensation is a self-condensation of ester in the presence of alkali alkoxide in alcohol to form β-keto esters. It is carried out under basic conditions to generate β-keto-esters. Some of the esters are reported not to undergo in this type of condensation under normal conditions with sodium ethoxide due to the steric hindrance. Some quaternary ammonium salts of long aliphatic chains has been used and reported to improve the yield of the reaction. This reaction is found to be very useful for the synthesis of a series of β-keto esters (both branched and unbranched). This reaction can also be useful in preparation of γ-diketones in reaction with epoxides followed by oxidation and decarboxylation.

Keywords:

  • β-keto esters;
  • steric hindrance;
  • mesitylmagnesium bromide;
  • γ-diketones