Sodium Benzoate → 3-(Benzoyloxy)-2,4-pentanedione

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Reaction Steps

Sodium benzoate (106.5 g, 0.74 mol) is suspended in 500 ml of dry DMSO in a three necked flask equipped with a mechanical stirrer and under a gentle stream of argon. Chloroacetylacetone (50 g, 0.37 mol) is then added and the resulting orange mixture is stirred vigorously. After 3 hours the reaction is complete (TLC hexane/ethyl acetate 8/2); the melange is cooled by means of iced water and diluted with 500 ml of water. The solution is then extracted into ether (3×400 ml), washed with water (2×1 L), dried over Na2SO4 and concentrated to dryness in vacuo. The resulting viscous orange oil is pure enough for the next step. The yield is 81.4 g (100%).

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