hydrogen; palladium dihydroxide in ethanol P=2068.6 Torr; 3 h;

ammonium acetate; sodium cyanoborohydride in methanol 89 h; Ambient temperature;

hydrogenchloride; palladium on activated charcoal in methanol P=2585.7 Torr; 36 h; Yield given;

palladium diacetate in dichloromethane

1: 81 percent / 2N aq. NaOH / 1.) 55 deg C, 2 h, 2.) reflux 2 h 2: 1.) Na, EtOH, 2.) 2N aq. HCl / 1.) reflux, 1 h, 2.) EtOH, reflux, 30 min 3: p-TsOH*H2O / benzene / 17 h / Heating 4: H2 / PtO2 / ethanol / 2.5 h / 1520 Torr 5: H2 / 10percent Pd/C / ethanol / 1 h / 45 °C / 2280 Torr View Scheme

1: 1.) Na, EtOH, 2.) 2N aq. HCl / 1.) reflux, 1 h, 2.) EtOH, reflux, 30 min 2: p-TsOH*H2O / benzene / 17 h / Heating 3: H2 / PtO2 / ethanol / 2.5 h / 1520 Torr 4: H2 / 10percent Pd/C / ethanol / 1 h / 45 °C / 2280 Torr View Scheme

1: 94 percent / SOCl2 / benzene / 3 h / Heating 2: 98 percent / diethyl ether / Ambient temperature 3: 19 percent / <Rh(CH3COO)2>2, CF3COOH / CH2Cl2 / 0.42 h / Heating 4: p-TsOH*H2O / benzene / 17 h / Heating 5: H2 / PtO2 / ethanol / 2.5 h / 1520 Torr 6: H2 / 10percent Pd/C / ethanol / 1 h / 45 °C / 2280 Torr View Scheme

1: 96 percent / H2 / 10percent Pd/C / aq. ethanol / 2660 Torr 2: 94 percent / SOCl2 / benzene / 3 h / Heating 3: 98 percent / diethyl ether / Ambient temperature 4: 19 percent / <Rh(CH3COO)2>2, CF3COOH / CH2Cl2 / 0.42 h / Heating 5: p-TsOH*H2O / benzene / 17 h / Heating 6: H2 / PtO2 / ethanol / 2.5 h / 1520 Torr 7: H2 / 10percent Pd/C / ethanol / 1 h / 45 °C / 2280 Torr View Scheme

1: 98 percent / diethyl ether / Ambient temperature 2: 19 percent / <Rh(CH3COO)2>2, CF3COOH / CH2Cl2 / 0.42 h / Heating 3: p-TsOH*H2O / benzene / 17 h / Heating 4: H2 / PtO2 / ethanol / 2.5 h / 1520 Torr 5: H2 / 10percent Pd/C / ethanol / 1 h / 45 °C / 2280 Torr View Scheme

1: 19 percent / <Rh(CH3COO)2>2, CF3COOH / CH2Cl2 / 0.42 h / Heating 2: p-TsOH*H2O / benzene / 17 h / Heating 3: H2 / PtO2 / ethanol / 2.5 h / 1520 Torr 4: H2 / 10percent Pd/C / ethanol / 1 h / 45 °C / 2280 Torr View Scheme