1: 98 percent / H2 / Pd/C / ethanol / 3 h / 20 °C / 2585.81 Torr 2: thionyl chloride; DMF / toluene; CH2Cl2 / 2 h / 20 °C 3: 28.6 g / NH4OH / tetrahydrofuran / 0.25 h / 0 °C 4: 45 percent / LiAlH4 / diethyl ether / 5.5 h / Heating View Scheme

1: 98 percent / H2 / Pd/C / ethanol / 3 h / 20 °C / 2585.81 Torr 2: 100 percent / LiAlH4 / tetrahydrofuran / Heating View Scheme

hydrogen; palladium on activated charcoal in ethanol T=20°C; Catalytic hydrogenation; P=2585.81 Torr; 3 h;