Benzyl Bromide → 3-(Benzyloxy)benzoic acid

Participants

Reaction Steps

A solution of methyl 3-hydroxybenzoate (1.00 g, 6.56 mmol)in THF was treated with sodium hydride (60% by wt in oil, 276 mg, 6.90 mmol). After 20 minutes, the mixture was treated with benzyl bromide (0.78 mL, 6.56 mmol) and then heated at reflux. The mixture was cooled, treated with saturated ammonium chloride and EtOAc. The layers were separated and the aqueous layer was washed with EtOAc (3×). The combined organic extracts were washed with saturated NaCl, dried over MgSO4 and concentrated. A solution of the crude material in dioxane (20 mL) was treated with 2.5 N NaOH (13 mL) and stirred vigorously. The mixture was acidified by addition of 5 N HCl and partitioned with EtOAc. The aqueous layer was washed with EtOAc (3×) and the combined extracts were dried (MgSO4) and concentrated yielding the title compound.

Provenance & Evidence