Benzyl Bromide → 2-Benzyloxy-6-methoxybenzoic Acid Benzyl Ester

Participants

Reaction Steps

While stirring a mixture of 6-methoxysalicylic acid (5.07 g, 30.15 mmol) and sodium hydride (60% w/w, 3.02 g, 75.38 mmol) under cooling with ice, DMF (30 mL) was added thereto. The mixture solution was stirred at the same temperature for 10 minutes, and then benzyl bromide (8.95 mL, 75.38 mmol) was added thereto over 5 minutes and the reaction mixture was stirred at the same temperature for 30 minutes and at room temperature for 2.5 hours. To the reaction mixture was added a saturated ammonium chloride aqueous solution and water under cooling with ice, and the mixture was extracted with ether. The organic layer was washed with water and a saturated ammonium chloride aqueous solution and dried (anhydrous sodium sulfate), and then the solvent was distilled under reduce pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:10 to 1:5)] to obtain the title compound (6.24 g, 59%).

Provenance & Evidence