1: sodium / 1.) EtOH, 45 deg C, 20 min, 2.) EtOH, a) from 25 deg C to 70 deg C, b) 85 deg C, 1 h 2: 85percent aq. KOH / 2 h / 90 - 100 °C View Scheme

1: 89 percent / NaBH4 / ethanol / 0.5 h 2: 75 percent / aq. KOH / a) reflux, 7 h, b) RT, overnight View Scheme

1: 100 percent / piperidine, benzoic acid / toluene / 3 h / Heating 2: 89 percent / NaBH4 / ethanol / 0.5 h 3: 75 percent / aq. KOH / a) reflux, 7 h, b) RT, overnight View Scheme

1: CCl4, Ph3P 2: (i) NaOMe, (ii) aq. KOH View Scheme

(i) NaOMe, (ii) aq. KOH; Multistep reaction;

1: 81 percent / 165 °C 2: thionyl chloride / 0.75 h / Heating 3: 93 percent / AlCl3 / CS2 / 3 h / Heating 4: 98 percent / NaBH4 / ethanol / 2 h / 25 °C 5: 92 percent / p-toluenesulfonic acid*H2O / benzene / 1 h / Heating 6: 96 percent / NiCl2<dppp>2 / diethyl ether / 22 h / Heating View Scheme

1: 81 percent / 165 °C 2: thionyl chloride / 0.75 h / Heating 3: 93 percent / AlCl3 / CS2 / 3 h / Heating 4: 98 percent / NaBH4 / ethanol / 2 h / 25 °C 5: 92 percent / p-toluenesulfonic acid*H2O / benzene / 1 h / Heating 6: 98 percent / NiCl2<dppp>2 / diethyl ether / Heating 7: 97 percent / H2 / PtO2 / tetrahydrofuran / 1034.3 Torr View Scheme

1: 81 percent / 165 °C 2: thionyl chloride / 0.75 h / Heating 3: 93 percent / AlCl3 / CS2 / 3 h / Heating 4: 98 percent / NaBH4 / ethanol / 2 h / 25 °C 5: 92 percent / p-toluenesulfonic acid*H2O / benzene / 1 h / Heating 6: 96 percent / NiCl2<dppp>2 / diethyl ether / 22 h / Heating 7: 98 percent / H2 / PtO2 / tetrahydrofuran / 1034.3 Torr View Scheme

1: 81 percent / 165 °C 2: thionyl chloride / 0.75 h / Heating 3: 93 percent / AlCl3 / CS2 / 3 h / Heating 4: 98 percent / NaBH4 / ethanol / 2 h / 25 °C 5: 92 percent / p-toluenesulfonic acid*H2O / benzene / 1 h / Heating 6: 99 percent / NiCl2<dppp>2 / diethyl ether / Heating 7: 97 percent / H2 / PtO2 / tetrahydrofuran / 1034.3 Torr View Scheme