Hydrochloric Acid → 3-Chloro-4-methylphenyl isopropyl sulfone

Participants

Reaction Conditions

Reaction Steps

99.1 g (0.5 mol) of isopropyl 4-methylphenyl sulfone in 180 g of 96% strength sulfuric acid are introduced into a 500 ml glass flask equipped with stirrer, condenser, gas inlet, thermometer and dropping funnel. At 70° C., about 140 g of chlorine are metered in over the course of 6 hours with vigorous stirring. After the reaction is completed, residual hydrogen chloride is eliminated by passing a N2 stream through the flask, 300 g of water are added dropwise and the mixture is allowed to cool to 20° C. in the course of 2 hours with stirring. The mixture is extracted four times each with 200 g of methylene chloride, the combined extracts are washed to neutrality using 5% strength NaHCO3 solution, dried with Na2SO4 and concentrated on a rotary evaporator. 66.7 g of 3-chloro-4-methylphenyl isopropyl sulfone are obtained (yellowish oil, content 94.3% by weight, corresponding to a yield of 54.1%, 1H-NMR (CDCl3): 7.3-7.9 (m, 3H); 3.23 (sp, 6.8 Hz, lH); 2.47 (s); 1.42 d, 6.8 Hz, 6H).

Provenance & Evidence