Standard Article

The Arndt-Eistert Synthesis

  1. W. E. Bachmann,
  2. W. S. Struve

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or001.02

Organic Reactions

Organic Reactions

How to Cite

Bachmann, W. E. and Struve, W. S. 2011. The Arndt-Eistert Synthesis. Organic Reactions. 1:2:38–62.

Author Information

  1. University of Michigan

Publication History

  1. Published Online: 15 MAR 2011

Chemistry Terms

Choose one or more boxes to highlight terms.

Abstract

The Arndt-Eistert synthesis is a procedure for converting an acid to its next highest homolog or to a derivative of the homologous acid, and an ester and an amide. The synthesis, which is applicable to both, aliphatic and aromatic acids involves the following three operations; formation of the acid chloride; reaction of the acid chloride with diazomethane to yield a diazoketone; and rearrangement of the diazoketone in the presence of suitable reagents and a catalyst (colloidal silver, platinum, copper). An acid is formed in the presence of water, and ester is produced in an alcohol, and am amide results when ammonia or an amine is used.

Keywords:

  • Arndt-Eistert synthesis;
  • diazomethane;
  • acids;
  • amides;
  • esters;
  • experimental conditions