thionyl chloride; sodium sulfate in water

thionyl chloride in diethyl ether 16 h; Ambient temperature;

1: 93 percent / POCl3/Na2CO3 / acetonitrile / 1.5 h / Heating 2: TsOH*2H2O / acetonitrile / Heating; Lewis acids instead TsOH*2H2O View Scheme

1: 88 percent / ethanol / 2 h / Heating 2: 85 percent / N-bromosuccinimide / CCl4 / 3 h / Heating; Irradiation 3: 70 percent / sodium ethoxide, 2-nitropropane / ethanol / 2 h / Heating 4: 41 percent / hydroxylamine hydrochloride / ethanol / 16 h / Ambient temperature 5: 61 percent / SOCl2 / diethyl ether / 16 h / Ambient temperature View Scheme

1: 93 percent / p-toluenesulfonic acid / 1.5 h / heated on stem bath 2: 88 percent / ethanol / 2 h / Heating 3: 85 percent / N-bromosuccinimide / CCl4 / 3 h / Heating; Irradiation 4: 70 percent / sodium ethoxide, 2-nitropropane / ethanol / 2 h / Heating 5: 41 percent / hydroxylamine hydrochloride / ethanol / 16 h / Ambient temperature 6: 61 percent / SOCl2 / diethyl ether / 16 h / Ambient temperature View Scheme

1: 85 percent / N-bromosuccinimide / CCl4 / 3 h / Heating; Irradiation 2: 70 percent / sodium ethoxide, 2-nitropropane / ethanol / 2 h / Heating 3: 41 percent / hydroxylamine hydrochloride / ethanol / 16 h / Ambient temperature 4: 61 percent / SOCl2 / diethyl ether / 16 h / Ambient temperature View Scheme

1: 41 percent / hydroxylamine hydrochloride / ethanol / 16 h / Ambient temperature 2: 61 percent / SOCl2 / diethyl ether / 16 h / Ambient temperature View Scheme

1: 70 percent / sodium ethoxide, 2-nitropropane / ethanol / 2 h / Heating 2: 41 percent / hydroxylamine hydrochloride / ethanol / 16 h / Ambient temperature 3: 61 percent / SOCl2 / diethyl ether / 16 h / Ambient temperature View Scheme

1: conc. ammonium hydroxide / ethyl acetate / 16 h / Ambient temperature 2: phosphorus oxychloride, potassium carbonate / acetonitrile / 3.5 h / Heating 3: p-toluenesulfonic acid monohydrate / acetonitrile / 16 h / Heating View Scheme

1: sodium nitrite / ethyl acetate; H2O / Ambient temperature 2: conc. ammonium hydroxide / ethyl acetate / 16 h / Ambient temperature 3: phosphorus oxychloride, potassium carbonate / acetonitrile / 3.5 h / Heating 4: p-toluenesulfonic acid monohydrate / acetonitrile / 16 h / Heating View Scheme