Chloroform → Ethanol, 2-methoxy-, 1-(4-methylbenzenesulfonate)

Participants

Reaction Steps

2-methoxyethanol (0.989 g, 13 mmol) was dissolved in 30 ml dichloromethane, and triethylamine (2.53 g, 25 mmol) was added to the solution. The reaction mixture was set to stir in an ice-water bath, and p-toluenesulfonyl chloride (3.22 g, 17 mmol) was added all at once. The ice was allowed to melt, and the reaction was continued overnight. The reaction mixture was then filtered, to remove all of the triethylamine hydrochloride, and the filtrate was washed with ml saturated NaHCO3(aq), then 30 ml 1N KHSO4(aq), then 30 ml saturated NaHCO3(aq). The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation. The colorless oily residue was chromatographed on silica gel in 1:5 ethyl acetate:chloroform, to yield 2.77 g (92% yield) of 2-methoxyethyl tosylate as a viscous liquid.

Provenance & Evidence