von Richter Reaction
Published Online: 15 SEP 2010
Copyright © 2010 John Wiley & Sons, Inc. All rights reserved.
Comprehensive Organic Name Reactions and Reagents
How to Cite
2010. von Richter Reaction. Comprehensive Organic Name Reactions and Reagents. 2911–2914.
- Published Online: 15 SEP 2010
The preparation of an aromatic carboxylic acid by treatment of a para- or meta-substituted aromatic nitro compound with potassium cyanide in aqueous alcoholic solution at high temperature, by which the carboxyl group occupies the position ortho to the eliminated nitro group is generally referred to as the von Richter reaction. This reaction has been found to take place exclusively at the ortho-position of the eliminated nitro group. Moreover, the von Richter reaction can be inhibited in the presence of potassium ferricyanide (K3Fe(CN)6) and sodium sulfite. The study proposes that this reaction involves an initial attack by cyanide ion at the ortho position of the nitro group in a fashion of a Michael addition, followed by aromatization with expulsion of the ortho-proton. This reaction has limited application in organic synthesis.
- potassium ferricyanide;
- Michael addition;