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Acetoacetic Ester Synthesis

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr003

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Acetoacetic Ester Synthesis. Comprehensive Organic Name Reactions and Reagents. 3:9–12.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

Synthesis of α-substituted acetic acid esters or substituted acetones from acetoacetic ester by treatment of ethyl acetoacetate with a strong base, followed by alkylation and subsequent deacetylation or decarboxylation is known as acetoacetic ester synthesis. The α-methylene proton is readily deprotonated, and the resulting α-carbanion can be alkylated or acylated because α-methylene protons in β-ketoesters are very acidic and possess pKa as low as 10. The acetoacetic esters can also be alkylated in acidic condition via the form of enol intermediate with the formation of the unexpected products. The new substituted β-ketoesters give substituted esters on treatment with concentrated base and give substituted acetones through decarboxylation on hydrolysis under mild conditions. This reaction has been used to synthesize 7-nitro-indole.

Keywords:

  • β-ketoesters;
  • decarboxylation;
  • 7-nitro-indole;
  • ethyl acetylacetate