thionyl chloride in benzene 5 deg C then 4 h reflux;

1: 92 percent / H2 / 10percent Pd/C / methanol / 2 h / 2280 Torr 2: 80 percent / SOCl2 / CH2Cl2 / 1.) room temp., overnight, 2.) reflux, 2 h View Scheme

1: 60 percent / LiAlH4 / diethyl ether / 5 h / 25 °C 2: 60 percent / SO2Cl2 / CHCl3 / 3 h / Heating View Scheme

1: 77 percent / 10percent aq. NaOH / CH2Cl2 / 4 h 2: 80 percent / dimethylformamide / 48 h / Ambient temperature 3: 74 percent / NaOMe / methanol / 0.08 h 4: 58 percent / Cs2CO3 / dimethylformamide / 24 h / 85 °C 5: 96 percent / HCl / methanol / 1 h / Ambient temperature View Scheme