Ethanol, 2-[(4-methylphenyl)sulfonyl]- → 3-Chlorosulfonyl-4-methylbenzoic acid 2-(p-tolylsulfonyl)ethyl ester

Participants

Reaction Steps

A heterogeneous mixture of 3-chlorosulfonyl-4-methylbenzoic acid (11.7 g, 50.0 mmol) in 18 mL of SOCl2 was refluxed for 3 h. After the excess of SOCl2 was removed, the residual brown oil was dissolved in 50 mL of CH3CN, and then 2-(p-tolylsulfonyl)ethanol (9.4 g, 47.0 mmol, 0.95 eq.) was added. The mixture was heated to reflux temperature for 24 h. Thereafter most of CH3CN was removed, the resulting oil was purified by short column chromatography (CH2Cl2 to 1% MeOH in CH2Cl2) to give a light brown oil, which solidified on standing. The solid was dried further under vacuum to yield 19.5 g (99%) of 3-chlorosulfonyl-4-methylbenzoic acid 2-(p-tolylsulfonyl)ethyl ester (Intermediate 49).

Provenance & Evidence