ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Oxidation of 4-nitro-o-xylene with nitric acid using N-hydroxyphthalimide under phase transfer conditions

Song-Bo Wei, Bo Tang, and Xin-Hua Peng

School of Chemical Engineering, Nanjing University of Science and Technology, Xiao Ling Wei No. 200, Nanjing 210094, China

E-mail: xhpeng@mail.njust.edu.cn

Abstract: 4-Nitro-o-xylene was selectively oxidized to 2-methyl-4-nitrobenzoic acid using dilute nitric acid as the oxidizing agent under atmospheric pressure. The oxidation of 4-nitro-o-xylene was effectively promoted by an addition of radical initiators. Under reflux, 2-methyl-4-nitrobenzoic acid was afforded in high yield using nitric acid combined with N-hydroxyphthalimide, cobalt dichloride (CoCl₂ · 6H₂O), manganese acetate (Mn(OAc)₂ · 4H₂O) and phase transfer catalyst

Keywords: 4-nitro-o-xylene – 2-methyl-4-nitrobenzoic acid – nitric acid – oxidation – phase transfer catalyst

Full paper is available at www.springerlink.com.

DOI: 10.1515/chempap-2015-0054

Chemical Papers 69 (4) 580–585 (2015)