thionyl chloride in dichloromethane T=0°C; Inert atmosphere;

sodium hydroxide in tetrahydrofuran; water

1.1: trichlorophosphate / 1,2-dichloro-ethane / 8 h / 0 °C / Inert atmosphere; Reflux 1.2: Inert atmosphere; Cooling with ice 2.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 3.1: thionyl chloride / dichloromethane / 0 °C / Inert atmosphere View Scheme

1: nitrous acid 2: benzene; hydrogen chloride View Scheme

hydrogenchloride; acetic acid

hydrogen; calcium carbonate; palladium on activated charcoal in ethyl acetate P=2585.7 Torr; 2 h; Ambient temperature;

sodium hydrogencarbonate; acetone