Benzyl Bromide → Methyl 4-(benzyloxy)-2-hydroxybenzoate

Participants

Reaction Steps

To a solution of methyl-2,4-dihydroxybenzoate (10 g, 59.5 mmol) in acetone (200 mL) at 0° C. is added K2CO3 (30 g, 217 mmol), followed by benzyl bromide (7.72 mL, 65 mmol). The solution is warmed to ambient temperature and stirred for 48 h. The mixture is filtered and the solvent removed under reduced pressure. The crude oil is dissolved in EtOAc and washed with water, saturated NaHCO3, and dried over sodium sulfate. The solvent is removed under reduced pressure and the solid purified by flash chromatography using hexane/EtOAc (10:1) to afford 4-benzyloxy-2-hydroxybenzoic acid methyl ester as a white powder: 1H NMR (CDCl3) δ 10.93 (s, 1H), 7.73 (d, J=9.09 Hz, 1H), 7.42-7.33 (m, 5H), 6.53-6.49 (m, 2H), 5.07 (s, 2H), 3.90 (s, 3H); (M+H)+=259.

Provenance & Evidence