2-Alkyl-1, 4-dimethoxybenzenes (1 a - d ) react with both concentrated HNO 3 and NH 4 NO 3 in glacial acetic acid to form only simple nitrated products, 2-alkyl-5-nitro-1, 4-dimethoxybenzenes (4 a - d ). However, in the case of 2-alkyl-5-t-butyl-1, 4-dimethoxybenzenes (2 a - d ) or 2, 5-di-t-butyl-1, 4-dibenzoxybenzene (3), the formation of products greatly depends upon both the properties of the employed nitrating agents and the structures of these reactants. According to the observed results, two possibilities for the reactions mechanism are proposed.