1: 85 percent / 2 h / 180 °C 2: 91 percent / SOCl2 / 45 h / Heating View Scheme

1: 75 percent / 171 °C 2: 69 percent / 48percent aq. HBr, HBr gas / 12 h / 100 °C 3: 69 percent / PBr3 / 1 h / Heating 4: 68 percent / diethyl ether 5: 41 percent / aq. Na2S / ethanol / 2 h / Heating 6: 60 percent / LiAlH4 / diethyl ether / 4 h / Heating View Scheme

T=180°C; 2 h;

1: 75 percent / 171 °C 2: 69 percent / 48percent aq. HBr, HBr gas / 12 h / 100 °C 3: 69 percent / PBr3 / 1 h / Heating 4: 68 percent / diethyl ether 5: 41 percent / aq. Na2S / ethanol / 2 h / Heating View Scheme

1: With sodium hydroxide in water T=20°C; 28 h; 2: With hydrogenchloride in water

1: malonic acid dimethyl ester With sodium methylate in N,N-dimethyl-formamide T=5°C; 2: 1-chloro-2-(2-chloroethoxy)ethane in N,N-dimethyl-formamide T=80 - 85°C; 20 h; 3: With hydrogenchloride; sodium hydroxide; water Product distribution / selectivity; more than 3 stages;

potassium hydroxide

ethanol; sodium ethanolate anschliessend Verseifen mit waessrig-alkoholischer Kalilauge;