Cl.[CH3:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH3:10])=[C:5]([CH3:11])[C:4]=1[OH:12].[OH:13]O>CCOCC.O.C(O)(=O)C>[CH3:11][C:5]1[C:4](=[O:12])[C:3]([CH3:2])=[C:8]([CH3:9])[C:7](=[O:13])[C:6]=1[CH3:10]To 30 mg of the catalyst prepared in the same manner as in Example 19, 100 mg of water was added and stirred, and then 5 ml of an acetic acid solution containing 1% of hydrochloric acid was added. While cooling the mixture with water, 500 mg of 2,3,5,6-tetramethylphenol and 1 g of a 31% hydrogen peroxide aqueous solution were added, and the mixture was stirred for 2.5 hours. After the completion of the reaction, the mixture was diluted with ether, and the catalyst was filtered and washed successively with a NaHCO3 aqueous solution and a saturated sodium chloride aqueous solution. The filtrate was dried over MgSO4 and then concentrated, and the residue was purified by silica gel chromatography by eluting it with a solvent mixture of hexane-dichloromethane (1:1), whereby 300 mg (55% yield) of tetramethylbenzoquinone was obtained.
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