Benzyl Bromide → Dibenzyloxybenzaldehyde

Participants

Reaction Steps

To a solution of 2,3-dihydroxybenzaldehyde (61, 25 g, 0.18 mol) in N,N-dimethylformamide (150 mL) tetrahydrofuran (250 mL), sodium hydride (7.24 g, 0.18 mol) was added at 0° C. under an atmosphere of nitrogen. The reaction mixture was allowed to warm to room temperature and was stirred at room temperature for 10 minutes. To the reaction mixture was then added benzyl bromide (54 mL, 0.45 mol). The reaction mixture was stirred at room temperature under an atmosphere of nitrogen for 3 hours, then cooled down to 0° C. Sodium hydride (8 g, 0.2 mol) was added to the reaction mixture. The reaction mixture was allowed to warm to room temperature and was stirred at room temperature overnight. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was collected, washed with brine, and dried over magnesium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with ethyl acetate in hexane to provide the compound as an off-white solid (128, 46.2 gm, 80%).

Provenance & Evidence