sodium methylate in methanol

in ethanol

in diethyl ether; 1,2-dichloro-ethane 1 h;

1: H2, NH3, Raney nickel / ethanol / 2 h / 50 °C / 3040 - 3800 Torr 2: conc. H2SO4 / 1 h / Ambient temperature 3: 71 percent / diethyl ether; 1,2-dichloro-ethane / 1 h View Scheme

1: benzyltrimethylammonium hydroxide / ethanol / Heating 2: H2, NH3, Raney nickel / ethanol / 2 h / 50 °C / 3040 - 3800 Torr 3: conc. H2SO4 / 1 h / Ambient temperature 4: 71 percent / diethyl ether; 1,2-dichloro-ethane / 1 h View Scheme

1: 99 percent / toluenesulfonic acid monohydrate / benzene / 5 h / Heating 2: benzyltrimethylammonium hydroxide / ethanol / Heating 3: H2, NH3, Raney nickel / ethanol / 2 h / 50 °C / 3040 - 3800 Torr 4: conc. H2SO4 / 1 h / Ambient temperature 5: 71 percent / diethyl ether; 1,2-dichloro-ethane / 1 h View Scheme

1: conc. H2SO4 / 1 h / Ambient temperature 2: 71 percent / diethyl ether; 1,2-dichloro-ethane / 1 h View Scheme

toluene-4-sulfonic acid in xylene 4 h; Heating; Yield given;