hydrogenchloride; acetic acid 4 h; Heating; Yield given;

1: 1) NaH, tert-butyl alcohol / 1) THF, 2 h, 2) THF, reflux, 4 h 2: conc. HCl, AcOH / 4 h / Heating View Scheme

1: 71 percent / 1.) NaH / dimethylsulfoxide / 1.) room temperature, 10 min, 2.) 50 deg C, 20 h 2: 80 percent / 1.) sodium borohydride, boron trifluoride etherate, 2.)H2O, NaOH; 30percent H2O2 / 1.) THF, room temperature, 3 h, 2.) overnight 3: Jones reagent / acetone / 2 h / Ambient temperature 4: diethyl ether 5: 38 percent / sodium / toluene / 5 h / Heating 6: HCl / tetrahydrofuran / 10 h / Ambient temperature 7: zinc dust, acetic acid, HCl / 75 - 80 °C 8: KOH, hydrazine hydrate / bis-(2-hydroxy-ethyl) ether / 1.) reflux, 2 h, 2.) 210 deg C, 2 h View Scheme