Sulfuric Acid → 2,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-

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A solution of 13.6 g (100 mmol) of 2,3,6-trimethylphenol in 40 ml of acetic acid and a solution of 73.7 g (240 mmol) of 50% by weight potassium peroxomonosulfate in 320 ml of water were simultaneously added dropwise to a stirred solution of 0.68 g (2.0 mmol) of iron 5,14-dihydrodibenzo[b,i][5,9,14,18]tetraaza[14]annulene and 0.5 ml of concentrated sulfuric acid in 50 ml of acetic acid at room temperature with cooling. The reaction mixture was then subjected to steam distillation. The distillate was extracted by shaking with methylene chloride. The organic phase was shaken with aqueous sodium bicarbonate solution and then with water, separated from the aqueous phase, dried over magnesium sulfate, filtered and concentrated to a yellow oil, which slowly solidifed. 11.1 g (74%) of 2,3,5-trimethyl-p-benzoquinone were obtained in the form of yellow oily crystals.

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