A hydrazine-free Wolff–Kishner reaction suitable for an undergraduate laboratory

Cranwell, P. B. ORCID: https://orcid.org/0000-0001-7156-5576 and Russell, A. T. (2016) A hydrazine-free Wolff–Kishner reaction suitable for an undergraduate laboratory. Journal of Chemical Education, 93 (5). pp. 949-952. ISSN 0021-9584 doi: 10.1021/acs.jchemed.5b00954

Abstract/Summary

A Wolff–Kishner reaction that does not require hydrazine has been developed. The reaction sequence has two steps; formation of a carbomethoxyhydrazone from methyl hydrazinocarboxylate and acetophenone, then decomposition of this intermediate by treatment with potassium hydroxide in triethylene glycol. Purification is by filtration through a plug of silica encased in the barrel of a plastic syringe. The reaction sequence can be completed within a day-long laboratory class (8 hours).