in tetrachloromethane

hydrogenchloride in ethanol 1 h; Heating; Yield given;

1: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 2: conc. HCl / ethanol / 1 h / Heating View Scheme

1: 62 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH2Cl2 / 0.5 h 2: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 3: conc. HCl / ethanol / 1 h / Heating View Scheme

1: thionyl chloride / toluene / 1 h / 80 °C 2: ethanol; H2O / 12 h / Heating 3: aq. KOH / ethanol / 3 h / Heating 4: polyphosphoric acid / toluene / 4 h / Heating 5: 62 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH2Cl2 / 0.5 h 6: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 7: conc. HCl / ethanol / 1 h / Heating View Scheme

1: polyphosphoric acid / toluene / 4 h / Heating 2: 62 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH2Cl2 / 0.5 h 3: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 4: conc. HCl / ethanol / 1 h / Heating View Scheme

1: LiAlH4 / diethyl ether; tetrahydrofuran / 4 h / Heating 2: thionyl chloride / toluene / 1 h / 80 °C 3: ethanol; H2O / 12 h / Heating 4: aq. KOH / ethanol / 3 h / Heating 5: polyphosphoric acid / toluene / 4 h / Heating 6: 62 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH2Cl2 / 0.5 h 7: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 8: conc. HCl / ethanol / 1 h / Heating View Scheme

1: aq. KOH / ethanol / 3 h / Heating 2: polyphosphoric acid / toluene / 4 h / Heating 3: 62 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH2Cl2 / 0.5 h 4: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 5: conc. HCl / ethanol / 1 h / Heating View Scheme

1: ethanol; H2O / 12 h / Heating 2: aq. KOH / ethanol / 3 h / Heating 3: polyphosphoric acid / toluene / 4 h / Heating 4: 62 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH2Cl2 / 0.5 h 5: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 6: conc. HCl / ethanol / 1 h / Heating View Scheme

1: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 2: conc. HCl / ethanol / 1 h / Heating View Scheme