Pyridine → 3-acetylphenyl benzoate

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Reaction Steps

Under an argon atmosphere, 3-hydroxyacetophenone (0.68 g, 5 mmol) was dissolved in dichloromethane (5 mL), and pyridine (2.0 mL, 25 mmol) and benzoyl chloride (0.70 mL, 6.0 mmol) were added thereto, and then, the mixture was stirred at room temperature for 4 hours. To the mixture, an aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was sequentially washed with a 2 mol/L aqueous sodium hydroxide solution, 2 mol/L hydrochloric acid, and saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 50/50) to give benzoic acid (3-acetylphenyl)ester (1.19 g, 4.96 mmol, yield: 99%).

Provenance & Evidence