hydrogen; platinum(IV) oxide in pentane T=0°C; 0.25 h;

palladium on activated charcoal T=200 - 230°C;

palladium on activated charcoal T=200 - 230°C; 4 h;

1: chromyl acetate / acetic acid / a) 10 deg C, 10 h, b) RT, overnight 2: 92 percent / NaBH4 / methanol / a) RT, 2 h, b) reflux, 3 h 3: 82 percent / iodine, iodosylbenzene / cyclohexane / 1.5 h / 40 - 45 °C 4: 259 mg / chromyl acetate / acetic anhydride / a) 10 deg C, 10 h, b) RT, overnight 5: 94 percent / LAH / diethyl ether / 5 h / Heating 6: 241 mg / pyridine / 5 h / Ambient temperature 7: 86 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 8: 20 percent / HCl / benzene / 4 h / 50 °C 9: 12 percent / H2 / Adams' catalyst / pentane / 0.25 h / 0 °C View Scheme

1: 259 mg / chromyl acetate / acetic anhydride / a) 10 deg C, 10 h, b) RT, overnight 2: 94 percent / LAH / diethyl ether / 5 h / Heating 3: 241 mg / pyridine / 5 h / Ambient temperature 4: 86 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 5: 20 percent / HCl / benzene / 4 h / 50 °C 6: 12 percent / H2 / Adams' catalyst / pentane / 0.25 h / 0 °C View Scheme

1: 92 percent / NaBH4 / methanol / a) RT, 2 h, b) reflux, 3 h 2: 82 percent / iodine, iodosylbenzene / cyclohexane / 1.5 h / 40 - 45 °C 3: 259 mg / chromyl acetate / acetic anhydride / a) 10 deg C, 10 h, b) RT, overnight 4: 94 percent / LAH / diethyl ether / 5 h / Heating 5: 241 mg / pyridine / 5 h / Ambient temperature 6: 86 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 7: 20 percent / HCl / benzene / 4 h / 50 °C 8: 12 percent / H2 / Adams' catalyst / pentane / 0.25 h / 0 °C View Scheme

1: 82 percent / iodine, iodosylbenzene / cyclohexane / 1.5 h / 40 - 45 °C 2: 259 mg / chromyl acetate / acetic anhydride / a) 10 deg C, 10 h, b) RT, overnight 3: 94 percent / LAH / diethyl ether / 5 h / Heating 4: 241 mg / pyridine / 5 h / Ambient temperature 5: 86 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 6: 20 percent / HCl / benzene / 4 h / 50 °C 7: 12 percent / H2 / Adams' catalyst / pentane / 0.25 h / 0 °C View Scheme

1: 241 mg / pyridine / 5 h / Ambient temperature 2: 86 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 3: 20 percent / HCl / benzene / 4 h / 50 °C 4: 12 percent / H2 / Adams' catalyst / pentane / 0.25 h / 0 °C View Scheme

1: 94 percent / LAH / diethyl ether / 5 h / Heating 2: 241 mg / pyridine / 5 h / Ambient temperature 3: 86 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 4: 20 percent / HCl / benzene / 4 h / 50 °C 5: 12 percent / H2 / Adams' catalyst / pentane / 0.25 h / 0 °C View Scheme

1: 86 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 2: 20 percent / HCl / benzene / 4 h / 50 °C 3: 12 percent / H2 / Adams' catalyst / pentane / 0.25 h / 0 °C View Scheme