in diethylene glycol dimethyl ether 24 h; Heating / reflux;

1: 98 percent / I2, Ph3P, imidazole / CH2Cl2 / 3 h / Ambient temperature 2: 1.) NaH / 1.) THF, 2.) THF, RT, 1 h 3: 96 percent / aq. KOH / ethanol / 7 h / Heating 4: 67 percent / bis-(2-hydroxy-ethyl) ether / 3 h View Scheme

1: 96 percent / aq. KOH / ethanol / 7 h / Heating 2: 67 percent / bis-(2-hydroxy-ethyl) ether / 3 h View Scheme

1: 1.) NaH / 1.) THF, 2.) THF, RT, 1 h 2: 96 percent / aq. KOH / ethanol / 7 h / Heating 3: 67 percent / bis-(2-hydroxy-ethyl) ether / 3 h View Scheme

thionyl chloride; pyridine in diethylene glycol dimethyl ether T=70°C; 24 h;

in methanesulfonic acid