1-Hexanol → Methanesulfonic acid, trifluoro-, hexyl ester

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Reaction Steps

Under a dry nitrogen atmosphere, a solution of 18.1 g (177 mmol) 1-hexanol (dried over 3A sieves) and 14.1 g (178 mmol) pyridine (dried over 3A sieves) in 80 mL carbon tetrachloride (dried over 3A sieves) was added over 1.25 hr to a solution of 50 g (180 mmol) trifluoromethanesulfonic anhydride in 50 mL dry carbon tetrachloride, while cooling in an ice-waterbath. After an additional 5 min, the mixture was filtered, and the solids were washed with cold carbon tetrachloride. The filtrate was evaporated, and the residue was distilled, giving 19.7 g (47.5%) of hexyl trifluoromethanesulfonate: bp 35°-36° C. (0.35-0.40 torr).

Provenance & Evidence