Synthesis 2001(11): 1645-1648
DOI: 10.1055/s-2001-16760
PAPER
© Georg Thieme Verlag Stuttgart · New York

Heterogeneous Permanganate Oxidation of Styrene and Cinnamic Acid Derivatives: A Simple and Effective Method for the Preparation of Benzaldehydes

Sheng Lai, Donald G. Lee*
Department of Chemistry, University of Regina, Regina, SK, S4S 0A2, Canada
Fax: +1(306)5854894; e-Mail: dglee@uregina.ca;
Further Information

Publication History

Received 8 January 2001
Publication Date:
28 September 2004 (online)

Abstract

Styrene and cinnamic acid derivatives yield correspondingly substituted benzaldehydes when oxidized by permanganate under heterogeneous conditions. Reaction of terminal aliphatic alkenes under similar conditions gives discouragingly low yields; however, ketones and ketols are obtained in very good yields from the oxidation of 2,2-disubstituted and trisubstituted alkenes, respectively. Alumina and Amberlite IR-120 can be used as solid supports in these reactions with equally good results.