tris (triphenylphosphine)rhodium(I) chloride in ethanol T=60°C; 2 h;

hydrogen; platinum(IV) oxide in tetrahydrofuran P=1034.3 Torr; Yield given;

1: thionyl chloride 2: 91 percent / AlCl3 / CS2 3: 89 percent / NaBH4 / ethanol / 25 °C 4: 97 percent / p-toluenesulfonic acid * H2O / benzene / Heating 5: 98 percent / NiCl2<dppp>2 / diethyl ether / Heating 6: H2 / PtO2 / tetrahydrofuran / 1034.3 Torr View Scheme

1: 95 percent / KOH / acetic acid; H2O; tetrahydrofuran 2: 85 percent / 165 °C 3: thionyl chloride 4: 91 percent / AlCl3 / CS2 5: 89 percent / NaBH4 / ethanol / 25 °C 6: 97 percent / p-toluenesulfonic acid * H2O / benzene / Heating 7: 98 percent / NiCl2<dppp>2 / diethyl ether / Heating 8: H2 / PtO2 / tetrahydrofuran / 1034.3 Torr View Scheme

1: 89 percent / NaBH4 / ethanol / 25 °C 2: 97 percent / p-toluenesulfonic acid * H2O / benzene / Heating 3: 98 percent / NiCl2<dppp>2 / diethyl ether / Heating 4: H2 / PtO2 / tetrahydrofuran / 1034.3 Torr View Scheme

1: 97 percent / p-toluenesulfonic acid * H2O / benzene / Heating 2: 98 percent / NiCl2<dppp>2 / diethyl ether / Heating 3: H2 / PtO2 / tetrahydrofuran / 1034.3 Torr View Scheme

1: 85 percent / 165 °C 2: thionyl chloride 3: 91 percent / AlCl3 / CS2 4: 89 percent / NaBH4 / ethanol / 25 °C 5: 97 percent / p-toluenesulfonic acid * H2O / benzene / Heating 6: 98 percent / NiCl2<dppp>2 / diethyl ether / Heating 7: H2 / PtO2 / tetrahydrofuran / 1034.3 Torr View Scheme

1: 98 percent / NiCl2<dppp>2 / diethyl ether / Heating 2: H2 / PtO2 / tetrahydrofuran / 1034.3 Torr View Scheme

1: 91 percent / AlCl3 / CS2 2: 89 percent / NaBH4 / ethanol / 25 °C 3: 97 percent / p-toluenesulfonic acid * H2O / benzene / Heating 4: 98 percent / NiCl2<dppp>2 / diethyl ether / Heating 5: H2 / PtO2 / tetrahydrofuran / 1034.3 Torr View Scheme

1: 74 percent / NaOEt / Heating 2: 95 percent / KOH / acetic acid; H2O; tetrahydrofuran 3: 85 percent / 165 °C 4: thionyl chloride 5: 91 percent / AlCl3 / CS2 6: 89 percent / NaBH4 / ethanol / 25 °C 7: 97 percent / p-toluenesulfonic acid * H2O / benzene / Heating 8: 98 percent / NiCl2<dppp>2 / diethyl ether / Heating 9: H2 / PtO2 / tetrahydrofuran / 1034.3 Torr View Scheme