Benzoic acid, 3-(chlorosulfonyl)- → 2-(4-Methylbenzene-1-sulfonyl)ethyl 3-(chlorosulfonyl)benzoate

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Reaction Steps

A heterogeneous mixture of 3-chlorosulfonyl-benzoic acid (11.0 g, 50.0 mmol) in 18 mL of SOCl2 was refluxed for 3 h. Thereafter the excess of SOCl2 was removed, the residual brown oil was dissolved in 60 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 20 h. Thereafter the most of CH3CN was removed, the resulting oil was purified by short column chromatography (silica gel, CH2Cl2) to give light brown oil, which was dried further under vacuum to yield 19.1 g (95%) of a light brown solid.

Provenance & Evidence