Synthesis of tetranitrotoluenes

AT Nielsen, SL Christian, AP Chafin…

Index: Nielsen, Arnold T.; Christian, Stephen L.; Chafin, Andrew P.; Wilson, William S. Journal of Organic Chemistry, 1994 , vol. 59, # 7 p. 1714 - 1718

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Citation Number: 7

Abstract

The synthetic scheme employed here was a modification of Holleman's oxidation route. Mixed acid nitration of the ethyl carbamate of m-toluidine gave the 2, 4, 6-trinitro derivative 10 in 88% yield. Hydrolysis of 10 occurred slowly in hot aqueous HzS04 (90-95" C, 6 h) to give an 88% yield of the trinitrotoluidine ll. lSJ7 Since peroxydisulfuric acid is such a powerful reagent for oxidation of polynitroanilines to polynitroaromatics (Caro's acid was ...