1: 94 percent / N-methylmorpholine N-oxide hydrate, OsO4 / acetone; H2O / 48 h / 23 °C 2: 97 percent / p-TsOH monohydrate / benzene 3: 1) 70percent HClO4, 2) DDQ / 1) CCl4, RT, 3 h, 2) benzene, RT, 3.5 h 4: 232 mg / NaOMe / methanol / 0.25 h / Ambient temperature View Scheme

1: 97 percent / p-TsOH monohydrate / benzene 2: 1) 70percent HClO4, 2) DDQ / 1) CCl4, RT, 3 h, 2) benzene, RT, 3.5 h 3: 232 mg / NaOMe / methanol / 0.25 h / Ambient temperature View Scheme

1: diethyl ether / 1) RT, 20 min, 2) reflux, 30 min 2: 1.31 g / 4 N HCl / benzene; H2O / 0.17 h 3: 94 percent / N-methylmorpholine N-oxide hydrate, OsO4 / acetone; H2O / 48 h / 23 °C 4: 97 percent / p-TsOH monohydrate / benzene 5: 1) 70percent HClO4, 2) DDQ / 1) CCl4, RT, 3 h, 2) benzene, RT, 3.5 h 6: 232 mg / NaOMe / methanol / 0.25 h / Ambient temperature View Scheme

1: 24.4 percent / diethyl ether / 1 h / Heating 2: 93 percent / zinc amalgame, aq. HCl / toluene / 62 h / Heating 3: 97.3 percent / polyphosphoric acid / 87 °C / 1) 1 min, 2) 30 min 4: diethyl ether / 1) RT, 20 min, 2) reflux, 30 min 5: 1.31 g / 4 N HCl / benzene; H2O / 0.17 h 6: 94 percent / N-methylmorpholine N-oxide hydrate, OsO4 / acetone; H2O / 48 h / 23 °C 7: 97 percent / p-TsOH monohydrate / benzene 8: 1) 70percent HClO4, 2) DDQ / 1) CCl4, RT, 3 h, 2) benzene, RT, 3.5 h 9: 232 mg / NaOMe / methanol / 0.25 h / Ambient temperature View Scheme

sulfuric acid Yield given;

hydrogenchloride 1.) PhH; Yield given. Multistep reaction;