Abstract
AbstractThe preparation of an aromatic carboxylic acid by treatment of apara‐ ormeta‐substituted aromatic nitro compound with potassium cyanide in aqueous alcoholic solution at high temperature, by which the carboxyl group occupies the positionorthoto the eliminated nitro group is generally referred to as the von Richter reaction. This reaction has been found to take place exclusively at theortho‐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 theorthoposition of the nitro group in a fashion of a Michael addition, followed by aromatization with expulsion of theortho‐proton. This reaction has limited application in organic synthesis.
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