[CH3:1]C1C=C(O)C=CC=1O.CC1C(C)=C(C=CC=1O)O.[CH3:20][C:21]1[C:22]([OH:30])=[C:23]([CH3:29])[C:24]([CH3:28])=[C:25]([CH:27]=1)[OH:26]>[O-2].[Cr+3].[O-2].[O-2].[Cr+3].CO>[CH3:20][C:21]1[C:22]([OH:30])=[C:23]([CH3:29])[C:24]([CH3:28])=[C:25]([OH:26])[C:27]=1[CH3:1]Into an autoclave (inner volume: 9 ml, made of SUS 316, equipped with a manometer) were charged 0.115 g of methylhydroquinone, 3.268 g of methanol and 4.6 mg of chromium oxide (manufactured by High Purity Chemicals). The reaction was started by elevating the temperature up to 350° C. with sand bath. The pressure during the reaction was 18 MPa. After 2 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 methylhydroquinone was 17% by mole, the selectivity of dimethylhydroquinone was 74% by mole and the selectivity of trimethylhydroquinone was 2% by mole. No tetramethylhydroquinone was produced.
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