Nitric Acid → 2-Amino-2-methyl-1-(4-nitrophenyl)propane sulfate

Participants

Reaction Steps

A slight modification in the procedure described previously [Lavin et al, J. Biol. Chem., Vol. 256, p. 11944 (1981)] enables direct isolation of the product instead of column chromatographic separation of ortho (20%) and para (80%) isomers, both of which are products of the nitration. 2-Amino-2-methyl-1-phenylpropane hydrochloride (97 g, 0.41 mol) was dissolved in concentrated H2SO4 (195 ml) and the solution was cooled in an ice bath. Nitric acid (70%, 40 ml, 56 g, 0.6 mol) was added with stirring while the temperature was kept under 10° C. and then the solution was stirred for an additional 20 min. Next the mixture was poured on ice (4 l), and after 16 h white crystals were filtered, washed with cold water and methanol, and dried in air. Yield: 71.3 g (56%); mp 293°-298° C. dec; Rf 0.24 (dichloro-methane-methanol-ammonia, 4:1:0.03).

Provenance & Evidence