An Alternative One-Step Procedure for the Conversion of Piperonal to Piperonylonitrile

James M. DeMott Jr. and Charles J. Kelley
School of Arts and Sciences, Massachusetts College of Pharmacy and Health Sciences, Boston, MA 02115
J. Chem. Educ., 2001, 78 (6), p 780
DOI: 10.1021/ed078p780
Publication Date (Web): June 1, 2001
History, Education, and Documentation

Abstract

An alternative procedure is presented for the conversion of piperonal to piperonylonitrile. The reaction of hydroxylamine hydrochloride with the aromatic aldehyde piperonal forms the intermediate oxime, which rapidly loses water to give the corresponding nitrile. The entire procedure can be performed in about one-half hour with almost quantitative yields. Advantages of this method include the shortened time required to complete the sequence, better overall yield owing to the shortening of the sequence by one step, and improvement in safety by the elimination of a potentially toxic reagent.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Feature):

The Microscale Laboratory

Keywords (Subject):

Microscale Lab
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  • Received: August 03, 2009

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