Reaction #2487

Reaction equation

chlorobenzene

aluminum chloride

p-toluenesulfonyl chloride

→

4-methyl-4'-chlorodiphenylsulfone

Solvents

water

Conditions

Workup

1. 1
   Filtrationthe obtained crystal was filtered off
2. 2
   Washwashed with n-hexane

Procedure

To 150 ml of chlorobenzene, 100.1 g (0.75 mol) of aluminum chloride was added, and further 143 g (0.75 mol) of p-toluenesulfonyl chloride was added dropwise over 1 hour. After stirred for 3 hours at 55° C., the reaction mixture was poured into 1.5 liter of water, and then the obtained crystal was filtered off and washed with n-hexane to obtain 140 g of the intended 4-methyl-4'-chlorodiphenylsulfone. NMR (heavy chloroform): δ7.9-7.8 (m, 4H), 7.5 (m, 2H), 7.3 (d, 2H), 2.4 (s, 3H).

Source