thionyl chloride in water; ethyl acetate; Petroleum ether

1: N-bromosuccinimide, AIBN / CCl4 / 24 h / Heating 2: KOH, n-Bu4NHSO4 / CHCl3; H2O / 1.) RT, 1 h, 2.) reflux, 30 min View Scheme

1: thionyl chloride 2: aqueous dioxane View Scheme

1: lithium alanate; diethyl ether 2: thionyl chloride 3: aqueous dioxane View Scheme

1: diethyl ether; sodium 2: thionyl chloride 3: aqueous dioxane View Scheme

potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate in chloroform; water 1.) RT, 1 h, 2.) reflux, 30 min;

1,4-dioxane

1: 87 percent / acetonitrile / 15 h / Irradiation 2: 86 percent / LiAlH4 / diethyl ether / 2 h / 0 °C 3: 83 percent / Me2SO, Ac2O / 96 h / Ambient temperature 4: aq. hydroxylamine hydrochloride, sodium acetate / ethanol / 3 h / Heating 5: 74 percent / SOCl2 / dimethylformamide / 10 °C View Scheme

sodium hydroxide