4-Bromophenol → 4-(4-Bromophenoxy)butanoic acid

Participants

Reaction Steps

4-Bromo-phenol (172 g, 1 mol), 4-bromo-butyric acid ethyl ester (212 g, 1.1 mol) and K2CO3 (250 g, 1.8 mol) was dissolved in DMF (1000 mL), the mixture was stirred at room temperature overnight. the solvent was removed and water was added to the residue, the mixture was extracted with ethyl acetate, the organic layer was washed with brine, and dried over Na2SO4 the solvent was removed, to the residue was added NaOH (3M, 1000 mol) and CH3OH (600 mL), the mixture was stirred at 70° C. for 30 minutes and concentrated, the residue was dissolved in H2O and the mixture was washed with diethylether, the aqueous layer was acidified with HCl, and the mixture was extracted with ethyl acetate, the organic layer was washed with brine, dried over Na2SO4 concentrated to give crude 4-(4-bromophenoxy)butanoic acid (239 g, 98%).

Provenance & Evidence