sodium hydroxide; sulfuric acid in ethanol; water

aluminium trichloride in dichloromethane 6 h; Ambient temperature;

1: AlCl3 / nitrobenzene 2: H2SO4 View Scheme

sulfuric acid

sodium hydroxide in ethanol 3 h; Ambient temperature;

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: 57.2 percent / 10percent Pd/C / decahydronaphthalene / 15 h / Heating 7: 85 percent / BBr3 / CH2Cl2 / 2.5 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 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

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: hexamethyldisilazane / CH2Cl2 / 1.) -10 deg C, 1 h, 2.) room temperature 9: 80 mg / N-methylmorpholine N-oxide hydrate, OsO4 / Triton B / 2-methyl-propan-2-ol; H2O / 1.67 h / 10 °C 10: 482 mg / dichlorodicyanobenzoquinone / benzene / 24 h / Ambient temperature 11: 37.6 percent / EtSH, AlCl3 / CH2Cl2 / 2 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: 57.2 percent / 10percent Pd/C / decahydronaphthalene / 15 h / Heating View Scheme