Standard Article

Acyloin Condensation

(Acyloin Reaction)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr004

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Acyloin Condensation. Comprehensive Organic Name Reactions and Reagents. 4:13–17.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

Acyloin condensation is the synthesis of symmetrical α-hydroxy ketones via the reductive condensation of esters in an inert solvent in the presence of sodium. In a few cases, this reaction is also referred to as acyloin reaction. The most common method used to make acyloin is the reductive condensation of aliphatic esters with sodium in inert solvents, such as ether, xylene or even in liquid NH3. Trimethylchlorosilane has been reported to improve the yield of this reaction. Intromolecular acyloin condensation from aliphatic diesters affords cyclic ketones of different ring sizes. This reaction has a great utility to synthesize cyclic ketones of intermediates to a large ring from diesters with long hydrocarbon chain between two ester groups.

Keywords:

  • α-hydroxy ketones;
  • α-dicarbonyl intermediate;
  • trimethylchlorosilane;
  • acyloin