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Reduction with Aluminum Alkoxides

(The Meerwein-Ponndorf-Verley Reduction)

  1. A. L. Wilds

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or002.05

Organic Reactions

Organic Reactions

How to Cite

Wilds, A. L. 2011. Reduction with Aluminum Alkoxides. Organic Reactions. 2:5:178–223.

Author Information

  1. University of Wisconsin

Publication History

  1. Published Online: 15 MAR 2011

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Abstract

Verley and Meerwein and Schmidt discovered independently that an aldehyde can be reduced to the primary alcohol by treatment with aluminum ethoxide in the presence of ethanol. The reduction of the aldehyde occurs at the expense of an equivalent amount of ethanol which is oxdized to acetaldehyde. The reaction is reversible, but the equilibrium can be shifted to the point of complete reduction by removal of the acetaldehyde with a stream of hydrogen or nitrogen. This has the additional advantage of preventing side reactions such as aldol condensation between the original aldehdye and acetaldehyde. This method of reduction with aluminum chloride was found applicable to several aldehydes, but to only a few ketones of special types. This mild and specific method of reducing carbonyl compounds became know as the Meerwein-Ponndorf-Verley reduction Lund later studied the scope and limitations of the reaction.

Keywords:

  • reduction;
  • aluminum alkoxides;
  • Meerwein-Ponndorf-Verley reduction;
  • aluminum isopropoxide;
  • carbonyl groups;
  • limitations;
  • side reactions;
  • keto esters;
  • hydroxy ketones;
  • alpha-bromoketones