hydrogenchloride; hydrogen; palladium on activated charcoal in methanol T=20°C; P=2250.18 - 3000.24 Torr; 15 h;

lithium aluminium tetrahydride in diethyl ether T=0 - 2°C; 1 h;

1: 80 percent / tris(4-methoxyphenyl)phosphine; dimethylcarbonate / Pd(OAc)2 / H2O; tetrahydrofuran / 24 h / 40 °C 2: 86 percent / NaH / tetrahydrofuran / 15 h / 0 - 20 °C 3: 36 percent / H2; cc.HCl / Pd/C / methanol / 15 h / 20 °C / 2250.18 - 3000.24 Torr View Scheme

1: 86 percent / NaH / tetrahydrofuran / 15 h / 0 - 20 °C 2: 36 percent / H2; cc.HCl / Pd/C / methanol / 15 h / 20 °C / 2250.18 - 3000.24 Torr View Scheme

1.1: Mg / diethyl ether 1.2: 81.2 percent / diethyl ether; benzene / 20 - 44 °C 2.1: 54 percent / KOH / ethane-1,2-diol / 3 h / Heating 3.1: 87 percent / LiAlH4 / diethyl ether / 1 h / 0 - 2 °C View Scheme

1: 54 percent / KOH / ethane-1,2-diol / 3 h / Heating 2: 87 percent / LiAlH4 / diethyl ether / 1 h / 0 - 2 °C View Scheme

1.1: Mg / diethyl ether 1.2: 81.2 percent / diethyl ether; benzene / 20 - 44 °C 2.1: 54 percent / KOH / ethane-1,2-diol / 3 h / Heating 3.1: 87 percent / LiAlH4 / diethyl ether / 1 h / 0 - 2 °C View Scheme