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The Acetoacetic Ester Condensation and Certain Related Reactions

  1. Charles R. Hauser,
  2. Boyd E. Hudson Jr.

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or001.09

Organic Reactions

Organic Reactions

How to Cite

Hauser, C. R. and Hudson, B. E. 2011. The Acetoacetic Ester Condensation and Certain Related Reactions. Organic Reactions. 1:9:266–302.

Author Information

  1. Duke University

Publication History

  1. Published Online: 15 MAR 2011

Abstract

The acetoacetic ester condensation consist in the reaction in the presence of certain bases, of an ester having hydrogen on the alpha carbon atom with a second molecule of the same ester or with another ester to form a beta-ketoester. The bases capable of effecting such reactions include sodium alkoxides, triphenylmethylsodium, sodium amide, certain Grignard reagents. Metallic sodium effects certain condensations, the sodium, alkoxide which is formed in the reaction mixture probably serves as the active condensing agents. The classical example of the acetoacetic ester reaction is the formation of acetoacetic ester itself by the condensation of ethyl acetate by means of sodium ethoxide.

Keywords:

  • acetoacetic ester;
  • condensation;
  • side reactions;
  • Dieckmann reaction;
  • acylation;
  • esters;
  • acid chlorides;
  • sodium;
  • experimental conditions