Water → 3,5-Dioxohexanoic acid

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The benzoquinone (4) (2 g) was dissolved in acetic anhydride (5 ml) and concentrated sulfuric acid (0.5 ml) was added slowly. The mixture was stirred in the dark at a temperature of 32° C. and monitored by HPLC. After a period of time of 44 h, the reaction was worked up by pouring into iced water (50 ml) and extracting with dichloromethane (3×20 ml). The combined organics were washed with bicarbonate solution (3×50 ml), water (100 ml), dried (MgSO4), filtered and evaporated to yield triacetate (5) which solidified (1.78 g).

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