thionyl chloride in benzene 1.5 h; Heating;

1: NaOEt / ethanol / 1)reflux 3.5h 2)stand overnight 2: HCl / acetic acid; H2O / 1)35 - 50 deg C 2)room temp., 48h 3: 80 percent / 10percentHCl / 6 h / Heating 4: 100 percent / NaBH4 / ethanol / 5 h / Heating 5: 89 percent / SOCl2 / benzene / 1.5 h / Heating View Scheme

1: 100 percent / NaBH4 / ethanol / 5 h / Heating 2: 89 percent / SOCl2 / benzene / 1.5 h / Heating View Scheme

1: HCl / acetic acid; H2O / 1)35 - 50 deg C 2)room temp., 48h 2: 80 percent / 10percentHCl / 6 h / Heating 3: 100 percent / NaBH4 / ethanol / 5 h / Heating 4: 89 percent / SOCl2 / benzene / 1.5 h / Heating View Scheme

1: 80 percent / 10percentHCl / 6 h / Heating 2: 100 percent / NaBH4 / ethanol / 5 h / Heating 3: 89 percent / SOCl2 / benzene / 1.5 h / Heating View Scheme