Carbon Tetrachloride → 2-CHLORO-1-(p-TOLYLSULFONYL)ETHYL m-TOLYL SULFIDE

Participants

Reaction Conditions

Reaction Steps

p-Tolyl vinyl sulfone (27.3 g, 0.150 mole) was dissolved in 100 ml of reagent carbon tetrachloride to give a clear solution at 32° C. Addition of 27.3 g (0.172 mole) of m-toluenesulfenyl chloride gave a bright red solution. The exothermic reaction raised the temperature to 44° C. in ten minutes. The color faded to bright orange in 16 hours. Several weeks' standing at room temperature in a closed flask produced crystals. Filtration gave 19.5 g of crude product m.p. 80°-97°. Recrystallization from 50 ml of ethyl acetate-pentane (7:3) gave 13.8 g (27%) of pure product, m.p. 99.5°-100.5°.

Provenance & Evidence