[C:1]1(C=CC(O)=CC=1)O.CC1C=C(O)C=CC=1O.CC1C(C)=C(C=CC=1O)O.[CH3:28][C:29]1[C:30]([OH:38])=[C:31]([CH3:37])[C:32]([CH3:36])=[C:33]([CH:35]=1)[OH:34]>[O-2].[O-2].[Mn+4].CO>[CH3:28][C:29]1[C:30]([OH:38])=[C:31]([CH3:37])[C:32]([CH3:36])=[C:33]([OH:34])[C:35]=1[CH3:1]Into an autoclave (inner volume: 9 ml, made of SUS 316, equipped with a manometer) were charged 0.105 g of hydroquinone (manufactured by Wako Pure Chemical Ind., Ltd.), 3.602 g of methanol and 1.3 mg of manganese dioxide (manufactured by High Purity Chemicals Co.). The reaction was started by elevating the temperature up to 350° C. with sand bath. The pressure during the reaction was 15 MPa. After 8 hours, the autoclave was quickly cooled and the reaction solution was taken out from the autoclave when the temperature was cooled back to the room temperature. The measurement according to the process described above revealed that the conversion of hydroquinone was 41% by mole, the selectivity of monomethylhydroquinone was 43% by mole, the selectivity of dimethylhydroquinone was 13% by mole and the selectivity of trimethylhydroquinone was 1% by mole. No tetramethylhydroquinone was produced.
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