Synlett 2006(12): 1956-1958  
DOI: 10.1055/s-2006-944231
LETTER
© Georg Thieme Verlag Stuttgart · New York

Three-Step Synthesis of Highly Substituted Phenols from 1,3-Dinitropropanes

Roberto Ballini*, Luciano Barboni*, Guido Giarlo, Alessandro Palmieri
Dipartimento di Scienze Chimiche, Università di Camerino, Via S. Agostino 1, 63032 Camerino, Italy
Fax: +39(0737)402297; e-Mail: roberto.ballini@unicam.it;
Further Information

Publication History

Received 13 February 2006
Publication Date:
24 July 2006 (online)

Zoom Image

Abstract

Reaction of 1,3-dinitropropanes with acrolein under heterogeneous conditions (neat Al2O3) gives dinitrocyclohexanols, which, by treatment with potassium carbonate followed by acidic work-up, allow access to nitrocyclohexenone derivatives. The latter, by reaction with phenyltrimethylammonium tribromide, concludes a three-step synthesis of nitro-dibromophenols in satisfactory yields.