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The Synthesis of Aldehydes from Carboxylic Acids

  1. Erich Mosettig

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or008.05

Organic Reactions

Organic Reactions

How to Cite

Mosettig, E. 2011. The Synthesis of Aldehydes from Carboxylic Acids. Organic Reactions. 8:5:218–257.

Author Information

  1. National Institutes of Health, U. S. Public Health Service, Department of Health, Education, and Welfare

Publication History

  1. Published Online: 15 MAR 2011

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Abstract

The Rosenmund reduction of acid chlorides to the corresponding aldehydes was discussed in volume 4 of this series. There are a number of other less direct methods by which carboxylic acids can be converted into aldehydes and the purpose of this chapter is to consider the more useful of these procedures. Three of these methods, the hydrolytic decomposition of Reissert's compounds, the method of Grundmann, and the reductive desulfurization of thiol esters require acid chlorides as intermediates and in the respect are competitive with the Rosenmund reduction of acid chlorides. In the fourth method method, the McFadyen and Stevens synthesis, acid chlorides may be used for the preparation of the intermediate acyl hydrazides. Two additional methods, (Sonn and Muller, and Stephen) are based on the intermediate imido chlorides. These methods listed appear to be the one ones developed to the point where further discussion is profitable.

Keywords:

  • aldehydes;
  • carboxylic acids;
  • Reissert's compounds;
  • Grundman method;
  • reductive desulfurization;
  • thio esters;
  • McFadyen and Stevens method;
  • Sonn and Muller method;
  • Stephen method;
  • nitriles;
  • controlled reduction;
  • amides;
  • lithium aluminum hydride