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

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Reaction Steps

A solution of 15.2 g (100 mmol) of 2,3,5-trimethylhydroquinone in 150 ml of acetic acid and 16.1 g (125 mmol) of 70% by weight aqueous tert-butyl hydroperoxide 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 40° C. 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. 11.7 g (78%) of 2,3,5-trimethyl-p-benzoquinone were obtained in the form of yellow oily crystals.

Provenance & Evidence