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Gattermann Aldehyde Synthesis

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr264

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Gattermann Aldehyde Synthesis. Comprehensive Organic Name Reactions and Reagents. 264:1202–1205.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The preparation of aromatic aldehydes containing hydroxyl or alkyloxyl groups on the aromatic ring by treatment of the aromatics with hydrogen cyanide and hydrogen chloride in anhydrous solvent (e.g., ether) with or without the presence of a Lewis acid (e.g., ZnCl2, AlCl3) as a catalyst, in which aldimine hydrochloride functions as an intermediate, is generally referred to as the Gattermann aldehyde synthesis or simply as the Gatterman synthesis. It has been found that pure zinc cyanide can work properly for this reaction in presence of a trace amount of KCl or NaCl. This reaction is useful in the preparation of aromatic aldehydes with hydroxyl, alkoxyl, and even mutli-alkyl groups, such as mesitaldehyde

Keywords:

  • Lewis acid;
  • zinc cyanide;
  • mesitaldehyde;
  • anhydrous hydrogen chloride