Trimethylhydroquinone → 2,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-

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To a solution of 2.0 g of trimethylhydroquinone in 300 ml of chloroform was added 10 g of lead (IV) oxide, and the mixed solution was stirred at room temperature for 30 hours and then lead (IV) oxide was filtered off and the reaction solution was concentrated under reduced pressure. The concentrate was combined with 150 ml of hexane, washed with 50 ml of a 0.5% sodium bicarbonate solution and then 50 ml of water, dried over anhydrous sodium sulfate, then concentrated under reduced pressure. After cooling in a freezer, the precipitating crystal was filtered and washed with a small amount of cold hexane to give 2,3,5-trimethylbenzoquinone as a yellow needle crystal. The yield was 1.6 g (82%).

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