Hydroxyphenylacetic acid → 4-Benzyloxyphenylacetic acid ethyl ester

Participants

Reaction Steps

A DMF (100 ml) suspension of 4-hydroxyphenylacetic acid (10.0 g, 55.5 mmols), benzyl bromide (7.93 ml, 66.6 mmols) and potassium carbonate (23.1 g, 167 mmols) was stirred at room temperature for 6 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out in vacuo, and the resulting crude product was purified by silica gel column chromatography (hexane alone to hexane:ethyl acetate=10:1) to obtain the entitled compound (14.6 g) as an oil.

Provenance & Evidence