anhydrous potassium sulfate; potassium hydrogensulfate; oxone in tetrahydrofuran; water Ambient temperature;

1: 87 percent / benzene / 1.) 8 deg C, 5 min, 2.) r.t., 1.5 h 2: 70 percent / ozone / CH2Cl2; methanol / -78 °C View Scheme

1: 2.) aq. NaOH / 1.) benzene, reflux, 48 h, 2.) water, 5 deg C, 6 min 2: 87 percent / benzene / 1.) 8 deg C, 5 min, 2.) r.t., 1.5 h 3: 70 percent / ozone / CH2Cl2; methanol / -78 °C View Scheme

1: 87 percent / benzene / 1.) 8 deg C, 5 min, 2.) r.t., 1.5 h 2: 70 percent / ozone / CH2Cl2; methanol / -78 °C View Scheme

1: 65 percent / CHCl3 / 26 h / 65 °C 2: 1.) 98 percent formic acid, 2.) NaBH3(CN) / 1.) 38 deg C, 1 h, 2.) 20 deg C, 2 h 3: 83 percent / ethanol / 16 h / 78 °C 4: 75 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating 5: 83 percent / 48 percent aq. HBr / 18 h / 120 °C View Scheme