Tetrahydrofuran → Methyl 4-(1-hydroxyethyl)benzoate

Participants

Reaction Steps

71.2 g (0.4 mol) of methyl 4-acetylbenzoate, 300 ml of tetrahydrofuran and 100 ml of ethanol were supplied into a four-necked flask equipped with a stirrer and a thermometer. Then 7.6 g (0.2 mol) of sodium boron hydride was added at 15°-25° C. over a period of 3 hours. The mixture was maintained at the same temperature for 5 hours and the resulting reaction solution was poured into ice-water and extracted twice with 400 ml of ethyl acetate. The organic layer was concentrated under reduced pressure to obtain 71.0 g of methyl 4-(1-hydroxyethyl)benzoate (IIII-1) in a 98.6% yield.

Provenance & Evidence