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: 97 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 4 h / Heating 2: thionyl chloride / toluene / 1 h / 80 °C 3: ethanol; H2O / 12 h / Heating 4: 76 percent / aq. KOH / ethanol / 3 h / Heating 5: 83 percent / polyphosphoric acid / toluene / 4 h / Heating 6: 95 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH2Cl2 / 0.5 h 7: 58 percent / pyridine hydrochloride / 0.5 h / 210 °C 8: 90 percent / K2CO3 / acetone / 3 h / Heating 9: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 10: conc. HCl / ethanol / 1 h / Heating View Scheme

1: ethanol; H2O / 12 h / Heating 2: 76 percent / aq. KOH / ethanol / 3 h / Heating 3: 83 percent / polyphosphoric acid / toluene / 4 h / Heating 4: 95 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH2Cl2 / 0.5 h 5: 58 percent / pyridine hydrochloride / 0.5 h / 210 °C 6: 90 percent / K2CO3 / acetone / 3 h / Heating 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: thionyl chloride / toluene / 1 h / 80 °C 2: ethanol; H2O / 12 h / Heating 3: 76 percent / aq. KOH / ethanol / 3 h / Heating 4: 83 percent / polyphosphoric acid / toluene / 4 h / Heating 5: 95 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH2Cl2 / 0.5 h 6: 58 percent / pyridine hydrochloride / 0.5 h / 210 °C 7: 90 percent / K2CO3 / acetone / 3 h / Heating 8: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 9: conc. HCl / ethanol / 1 h / Heating View Scheme

1: 76 percent / aq. KOH / ethanol / 3 h / Heating 2: 83 percent / polyphosphoric acid / toluene / 4 h / Heating 3: 95 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH2Cl2 / 0.5 h 4: 58 percent / pyridine hydrochloride / 0.5 h / 210 °C 5: 90 percent / K2CO3 / acetone / 3 h / Heating 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: 95 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH2Cl2 / 0.5 h 2: 58 percent / pyridine hydrochloride / 0.5 h / 210 °C 3: 90 percent / K2CO3 / acetone / 3 h / Heating 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: 90 percent / K2CO3 / acetone / 3 h / Heating 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: 83 percent / polyphosphoric acid / toluene / 4 h / Heating 2: 95 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH2Cl2 / 0.5 h 3: 58 percent / pyridine hydrochloride / 0.5 h / 210 °C 4: 90 percent / K2CO3 / acetone / 3 h / Heating 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: 58 percent / pyridine hydrochloride / 0.5 h / 210 °C 2: 90 percent / K2CO3 / acetone / 3 h / Heating 3: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 4: conc. HCl / ethanol / 1 h / Heating View Scheme