Hydrochloric Acid → Ethyl (3-chlorobenzoyl)acetate

Participants

Reaction Steps

To a solution of 3-chloroacetophenone (23.9 g, 154 mmol) in diethyl carbonate (150 ml) was added ethanol (0.3 ml), and sodium hydride (60% in oil, 12.4 g, 309 mmol) was added under ice-cooling. The mixture was stirred at room temperature for 2 hrs. To the reaction solution was added 6N hydrochloric acid to stop the reaction, and water (500 ml) was added. Then, the mixture was extracted with ethyl acetate (500 ml×2). The extract was washed successively with water and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1-5:1) to give the objective substance (24.8 g, 71%).

Provenance & Evidence