1: 90 percent / H2 / Pt/C / ethanol / 3102.9 Torr / Ambient temperature 2: 65 percent / 1) LAH / diethyl ether / 1) kept overnight 2) 2 h reflux 3: 83 percent / triethylamine / CH2Cl2 / 0.5 h / -5 °C 4: 70 percent / benzene / 10 h / Heating 5: 60 percent / KOH / methanol; H2O / 4 h / Heating 6: 80 percent / tetrahydrofuran / 1.) r.t. 2.) reflux 2 h View Scheme

1: 90 percent / H2 / Pt/C / ethanol / 3102.9 Torr / Ambient temperature 2: 65 percent / 1) LAH / diethyl ether / 1) kept overnight 2) 2 h reflux 3: 83 percent / triethylamine / CH2Cl2 / 0.5 h / -5 °C 4: 70 percent / benzene / 10 h / Heating 5: 60 percent / KOH / methanol; H2O / 4 h / Heating View Scheme

1: 90 percent / H2 / Pt/C / ethanol / 3102.9 Torr / Ambient temperature 2: 65 percent / 1) LAH / diethyl ether / 1) kept overnight 2) 2 h reflux 3: 83 percent / triethylamine / CH2Cl2 / 0.5 h / -5 °C 4: 70 percent / benzene / 10 h / Heating 5: 60 percent / KOH / methanol; H2O / 4 h / Heating 6: 80 percent / tetrahydrofuran / 1.) r.t. 2.) reflux 2 h 7: 72 percent / 1) PTS monohydrate / acetic acid / 1.) 30 min, 0 deg C 2.) 30 min, r.t. View Scheme

lithium aluminium tetrahydride in tetrahydrofuran T=-78 - 25°C; 4 h; Inert atmosphere;