[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12](O)=O.C1(O)C2C(=CC=CC=2)C=CC=1.[H][H]>[O-2].[Cr+3].[O-2].[O-2].[Cr+3].CO>[CH3:12][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]=1[OH:1]Inoue et al (Chem. Pharm. Bull., 24 (9), 2199-2203, 1976) disclose ferric oxide and chromium oxide to be new alkylating catalyst of phenols. The activity and selectivity of these oxide catalysts were examined by liquid-phase reaction. 1-Naphthol, methanol and ferric oxide were charged in an autoclave equipped with a magnetic stirrer. After air in the autoclave was replaced by hydrogen, the temperature was raised to 400° C. over a period of 45 to 50 minutes. At such temperature, the pressure reached 100 atm. After 3 hours. 2-methyl-1-naphthol was produced in a conversion of 57.6 mol %. The remainder was starting material.
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