hydrogen; palladium hydroxide/carbon in methanol P=3040.2 Torr; 5 h;

1: lithium aluminium tetrahydride / diethyl ether / 0 - 20 °C 2: triethylamine / dichloromethane / 20 °C 3: acetonitrile / Reflux View Scheme

1: 85 percent / diethyl ether / 1 h / Heating; 1.) room temp., 15 min. 2: 83 percent / 3 h / 235 - 245 °C 3: 69 percent / conc. hydrochloric acid / 1 h / Heating 4: 1.) ethyl chloroformate, triethylamine / 1.) benzene, ether, 0 deg C, 15 min; 2.) benzene, ether, room temp. 20 min View Scheme

1: 81 percent / diethyl ether / 1 h / Heating; room temp., 15 min. 2: 75 percent / 18percent hydrochloric acid / H2O / 1.5 h 3: 1.) ethyl chloroformate, triethylamine / 1.) benzene, ether, 0 deg C, 15 min; 2.) benzene, ether, room temp. 20 min View Scheme

1: 85 percent / diethyl ether / 1 h / Heating; 1.) room temp., 15 min. 2: 83 percent / 3 h / 235 - 245 °C 3: 69 percent / conc. hydrochloric acid / 1 h / Heating View Scheme

1: 100 percent / diethyl ether / 1 h / Heating; 1.) room temp., 15 min. 2: 55 percent / 18percent hydrochloric acid / H2O / 1.5 h / Heating View Scheme

lithium aluminium tetrahydride in diethyl ether T=0 - 20°C;