Tetrahedron letters

p-Toluenesulfonic acid catalyzed regiospecific nitration of phenols with metal nitrates

V Anuradha, PV Srinivas, P Aparna, JM Rao

Index: Anuradha; Srinivas; Aparna; Rao, J. Madhusudana Tetrahedron Letters, 2006 , vol. 47, # 28 p. 4933 - 4935

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Citation Number: 71

Abstract

Highly regiospecific mononitration of phenols and substituted phenols is accomplished employing a metal nitrate and a catalytic amount of p-toluenesulfonic acid in acetone. An exclusive ortho-selectivity was observed with excellent yields. A variety of metal nitrates were used to obtain o-nitrophenols exclusively in good to excellent yields. The use of p- toluenesulfonic acid is key for the selectivity observed.