Toluene → Benzenesulfonyl chloride

Participants

Reaction Steps

A reactor was charged with 29.3 g of sodium benzenesulfinate (0.14 mole) obtained by the fourth step, and the benzenesulfinate was dissolved in 65 mL of water. Then, 105 mL of toluene was charged, and 10.3 g (0.1456 mole, 1.04 times moles) of chlorine was, little by little, blown into the reactor at a temperature of 18 to 20° C. The reaction solution was aged at the same temperature of 18 to 20° C. with stirring, and separated into an organic layer and an aqueous layer. The organic layer was washed with 90 g of a 3% aqueous sodium chloride solution and then concentrated at a reduced pressure and 45° C. or less to obtain 32.9 g of a benzenesulfonyl chloride solution. Gas chromatographic quantitative analysis revealed that the concentration of benzenesulfonyl chloride in the organic layer was 70.7% (weight; 24.21 g, 0.1371 mole), and the yield was 93.9%

Provenance & Evidence