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The Stobbe Condensation

  1. William S. Johnson,
  2. Guido H. Daub

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or006.01

Organic Reactions

Organic Reactions

How to Cite

Johnson, W. S. and Daub, G. H. 2011. The Stobbe Condensation. Organic Reactions. 6:1:1–73.

Author Information

  1. University of Wisconsin

Publication History

  1. Published Online: 15 MAR 2011

Chemistry Terms

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Abstract

In 1893, Stobbe demonstrated that when a mixture of acetone and diethyl succinate was treated with sodium ethoxide the expected acetoacetic ester type of condensation to give beta-diketo compound did not take place. The reaction of aldehydes or ketones with an ester of succinic acid to form alkylidenesuccinic acid, or isomers formed by a tautomeric shift of hydrogen, is known as the Stobbe condensation. One mole of metal alkoxide is required per mole of carbonyl compound and ester, and the primary product is the salt of the half-ester.

Keywords:

  • Stobbe condensation;
  • aldehydes;
  • ketones;
  • diketones;
  • keto esters;
  • cyano ketones;
  • isolation of products;
  • substituted succinic esters;
  • side reactions;
  • experimental procedures