Boron tribromide → 4-(4-Hydroxyphenyl)butanoic acid

Participants

Reaction Steps

To a solution of 1.00 g (5.15 mmol) of 4-(4-methoxyphenyl)butyric acid in 100 mL of dichloromethane at 0° C. was added 15.5 mL (15.5 mmol) of boron tribromide and the reaction was then allowed to warm to room temperature and stirred for 2 h. The reaction mixture was then poured into 200 mL of saturated sodium bicarbonate solution and the organic layer was separated. The aqueous layer was acidified with concentrated HCl solution and then extracted with dichloromethane. The combined organics were dried over MgSO4, filtered and concentrated in vacuo to provide 0.696 g of impure 4-(4-hydroxyphenyl)butyric acid.

Provenance & Evidence