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

nickel in diethyl ether 0.25 h; Heating;

lithium aluminium tetrahydride; isopropyl alcohol in diethyl ether T=-60 - -50°C;

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: 82 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: 82 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: 82 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: 82 percent / H2 / Adams' catalyst / pentane / 0.25 h / 0 °C View Scheme

1: 12.0 g / pyridine / 1.5 h / 25 °C 2: SeO2 / ethanol; pyridine / 1 h / Heating 3: NaBH4 / diethyl ether; methanol / 1 h 4: 19 percent Chromat. / BF3-etherate / CH2Cl2 / 0.5 h 5: 79 percent / H2 / PtO2 / ethanol / 10 h / 760 Torr / Ambient temperature 6: 48 percent / RuO2*xH2O/NaIO4 / CCl4 / 2.5 h / 20 °C 7: 5 mg / K2CO3 / m-xylene / 5 h / Heating 8: diisopropylamine/n-BuLi / hexane; tetrahydrofuran / 1.5 h 9: NaIO4 / CH2Cl2; H2O / 0.58 h / Ambient temperature 10: toluene / 5 h / Heating 11: 77 percent / DIBAL / tetrahydrofuran / 20 h 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: 82 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: 82 percent / H2 / Adams' catalyst / pentane / 0.25 h / 0 °C View Scheme