Benzoyl Peroxide → Methyl 2-[3-(methoxymethyl)phenyl]acetate

Participants

Reaction Steps

To a solution of ethyl(3-(bromomethyl)phenyl)acetate (1.78 g) in carbon tetrachloride (80 ml), 1.78 g of N-bromosuccinimide and 100 mg of benzoyl peroxide were added, and the reaction solution was heated overnight at reflux. The reaction solution was cooled, then the solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-10:90)) to afford a crude product. To a solution of the crude product (304 mg) in methanol (1 ml), 0.3 ml of sodium methoxide (25% methanol solution) was added, and the reaction solution was stirred at room temperature for 1.5 hours. The reaction solution was diluted with ethyl acetate, washed with a saturated aqueous ammonium chloride solution and a saturated saline solution sequentially, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by preparative thin layer chromatography (Kieselgel™ 60 F254, Art5744, made by Merck & Co., ethyl acetate/hexane (20:80)) to afford the title compound as a colorless oil.

Provenance & Evidence