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 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: 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

pyridinium chlorochromate in dichloromethane 1.5 h; Ambient temperature;

sodium dichromate; sulfuric acid; water in diethyl ether 0.5 h; Ambient temperature;