4-Toluenesulfonyl chloride → Cyclohexyl p-toluenesulfonate

Participants

Reaction Steps

5.0 g (0.05 mol) cyclohexanol and 11.2 g (0.1 mol) 1,4-diazabicyclo[2.2.2]octane are added to 50 mL ethyl acetate. This solution is cooled in an ice bath and 14.3 g (0.075 mol) tosyl chloride in 30 ml ethyl acetate is added drop-wise over 15 minutes. The ice bath is removed and the mixture is allowed to stir at room temperature for 4 days. After this time the solid precipitate is filtered and washed. The ethyl acetate filtrate and washings are then combined and washed successively with 10% HCl, saturated aq NaHCO3 and brine. The ethyl acetate is then evaporated and the resulting oil is purified by column chromatography to yield 11.5 g (90%) of cyclohexyl-p-toluenesulfonate.

Provenance & Evidence