Synthesis of Trinitroaromatics Using Alternative Mixed Acid Nitration Conditions

Conditions for the mild and efficient nitration of phloroglucinol (1,3,5-trihydroxybenzene), 5-methoxyresorcinol, 3,5-dimethoxyphenol, and 1,3,5-trimethoxybenzene have been developed. Yields of the trinitro derivatives are excellent (∼90%) for systems having one or more hydroxyl groups, and in the case of 1,3,5-trimethoxybenzene, the trinitro analog was obtained in 62% yield. The optimum nitration conditions utilize sulfuric acid (94–98%) and an inorganic nitrate salt.