Water → 4-(Octadecyloxy)-alpha-oxobenzeneacetic acid

Participants

Reaction Steps

To 2.9 g (6.45 mmol) of 4-(octadecyloxy)-alpha-oxobenzeneacetic acid ethyl ester in 200 ml of hot methanol was added 7.1 ml (7.1 mmol) of 1.0 N NaOH. The reaction mixture was stirred at reflux for 5 minutes, 50 ml of water was added and the solvents were removed at reduced pressure. Water (300 ml) was added and the product was extracted with methylene chloride-THF (4:1). The dried extract was concentrated at reduced pressure and the residual solid was recrystallized from acetone-hexane to give 2.39 g (88% yield, mp 78°-80°) of 4-(octadecyloxy)-alpha-oxobenzeneacetic acid.

Provenance & Evidence