Benzyl Bromide → HCID 11448276, compound

Participants

Reaction Steps

To a solution of methyl 3,4-dihydroxybenzoate (10.0 g, 59.4 mmol) in acetone (400 mL) was added potassium carbonate (8.21 g, 59.5 mmol). The mixture was stirred at room temperature (rt) for 30 minutes (min). To the resulting mixture was added benzyl bromide (7 mL, 59.4 mmol) in acetone (200 mL) dropwise over 2 hours (h) and stirring was continued for 48 h. Acetone was removed under vacuum and the resulting residue was partitioned between water (100 mL) and ethyl acetate (3×25 mL). The organic layer was dried over NaSO4, concentrated under vacuum and the resulting crude material purified via column chromatography to afford the product 30 (8.00 g, 52%). 1H NMR (300 MHz, CDCl3): δ 7.70 (m, 2H), 7.50 (m, 5H), 6.95 (m, 1H), 5.70 (s, 1H), 5.10 (s, 2H), 3.93 (s, 3H). MS (M+H): 259.

Provenance & Evidence