Sulfuric Acid → 2,4-Dimethyl-3-nitrophenol

Participants

Reaction Conditions

Reaction Steps

2,4-dimethyl-3-nitroaniline (105.6 g) is added to a reaction mixture containing 300 ml of H2SO4 and 300 ml of H2O. The reaction mixture is stirred at a temperature of 105°-108° C. for one half hour and then cooled to 0° C. A solution of sodium nitrite (52.6 g) in H2O (124 ml) is added dropwise. After addition is complete the reaction mixture is poured into a 50% aqueous H2SO4 solution (2,000 ml) and refluxed for one and one half hours. The reaction mixture is cooled over the weekend to ambient temperature, and filtered leaving a yellow and black solid which is washed with H2O, dried and boiled with hexanes (8 l). The hexane extract is concentrated and filtered to obtain 65.4 grams of a yellow solid, M.P. 99°-101° C.

Provenance & Evidence