[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:8]1[CH2:13][CH2:12][O:11]CC1.OO>C1COC(N2C(=O)NC(=O)C(F)=C2)C1.O>[C:1]1([CH:6]=[CH:5][C:4]([OH:8])=[CH:3][CH:2]=1)[OH:7].[C:13]1([C:12](=[CH:6][CH:1]=[CH:2][CH:3]=1)[OH:11])[OH:8]A stirrer, a cooler and a temperature indicator were provided to a four-necked flask having an internal volume of 200 ml; to this flask, 13.0 g of phenol, 4.0 g of 1,4-dioxane, 6.0 g of water and 1.3 g of TS-1 catalyst, prepared according to the above described procedure, were added, and heated to 70° C. by an oil bath. After the temperature of the mixture reached 70° C., 3.0 g of 31 weight % of hydrogen peroxide was added dropwise using a quantitative pump over 2 hours, and stirred further for 20 minutes after the addition. The reaction solution was analyzed by liquid chromatography, and the yields of hydroquinone and catechol were calculated. The results are shown in Table 1.
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