1: 98 percent / KOH / ethanol; H2O / 6 h / Heating 2: 95 percent / 170 °C View Scheme

1: 98 percent / KOH / ethanol; H2O / 6 h / Heating 2: 95 percent / 170 °C 3: thionyl chloride / 0.75 h / Heating 4: 85 percent / AlCl3 / CS2 / 3 h / Heating View Scheme

tetrakis(triphenylphosphine) palladium(0); sodium hydride 1.) DMF, 0 deg C, 2.) from 130 to 135 deg C; Yield given. Multistep reaction;

1: 98 percent / KOH / ethanol; H2O / 6 h / Heating 2: 95 percent / 170 °C 3: thionyl chloride / 0.75 h / Heating 4: 85 percent / AlCl3 / CS2 / 3 h / Heating 5: 89 percent / NaBH4 / ethanol; tetrahydrofuran 6: 96 percent / p-toluenesulfonic acid / benzene / Heating 7: 98 percent / NiCl2<dppp>2 / diethyl ether / Heating 8: 99 percent / H2 / PtO2 / tetrahydrofuran / 1034.3 Torr View Scheme

1: 98 percent / KOH / ethanol; H2O / 6 h / Heating 2: 95 percent / 170 °C 3: thionyl chloride / 0.75 h / Heating 4: 85 percent / AlCl3 / CS2 / 3 h / Heating 5: 89 percent / NaBH4 / ethanol; tetrahydrofuran 6: 96 percent / p-toluenesulfonic acid / benzene / Heating 7: 98 percent / NiCl2<dppp>2 / diethyl ether / Heating 8: 97 percent / H2 / PtO2 / tetrahydrofuran / 1034.3 Torr View Scheme

1: 98 percent / KOH / ethanol; H2O / 6 h / Heating 2: 95 percent / 170 °C 3: thionyl chloride / 0.75 h / Heating 4: 85 percent / AlCl3 / CS2 / 3 h / Heating 5: 89 percent / NaBH4 / ethanol; tetrahydrofuran 6: 96 percent / p-toluenesulfonic acid / benzene / Heating View Scheme

1: 98 percent / KOH / ethanol; H2O / 6 h / Heating 2: 95 percent / 170 °C 3: thionyl chloride / 0.75 h / Heating View Scheme

1: 98 percent / KOH / ethanol; H2O / 6 h / Heating 2: 95 percent / 170 °C 3: thionyl chloride / 0.75 h / Heating 4: 85 percent / AlCl3 / CS2 / 3 h / Heating 5: 89 percent / NaBH4 / ethanol; tetrahydrofuran View Scheme

1: 98 percent / KOH / ethanol; H2O / 6 h / Heating 2: 95 percent / 170 °C 3: thionyl chloride / 0.75 h / Heating 4: 85 percent / AlCl3 / CS2 / 3 h / Heating 5: 89 percent / NaBH4 / ethanol; tetrahydrofuran 6: 96 percent / p-toluenesulfonic acid / benzene / Heating 7: 97 percent / NiCl2<dppp>2 / diethyl ether / Heating 8: 98 percent / H2 / PtO2 / tetrahydrofuran / 1034.3 Torr View Scheme