Ethanol → Ethyl 4-benzyloxyphenethyl sulfonate

Participants

Reaction Conditions

Reaction Steps

To a solution of sodium 4-benzyloxyphenethyl sulfonate (4.84 g) and dimethylformamide (0.5 ml) in toluene (40 ml) is added dropwise thionyl chloride (1.35 ml) and the mixture heated at 90° C. for about 5 hours. The mixture is cooled to room temperature and is added portionwise to a solution of absolute ethanol (30 ml) and pyridine (15 ml) at -20° C. The mixture is stirred for 5 hours while being allowed to warm to 0° C. The mixture is diluted with ethyl acetate and 10% aqueous hydrochloric acid. The organic layer is washed with dilute HCl, water, saturated sodium bicarbonate solution, brine, dried over magnesium sulfate, filtered and concentrated in vacuo to give ethyl 4-benzyloxyphenethyl sulfonate.

Provenance & Evidence