hydrogen; palladium on activated charcoal in ethanol

1: 65 percent / benzene / Heating 2: 71 percent / (Et2AlH2)Na / toluene; tetrahydrofuran 3: 74 percent / Et3N / benzene 4: 84 percent / benzene / 1 h / Ambient temperature 5: 91 percent / H2 / 10percent Pd-C / ethanol 6: 62 percent / PPA / xylene; CHCl3 / 100 °C 7: NaBH4 / ethanol 8: 71 percent / 10percent H2SO4 / H2O / Heating 9: 91 percent / H2 / 10 percent Pd-C / ethanol View Scheme

1: 74 percent / Et3N / benzene 2: 84 percent / benzene / 1 h / Ambient temperature 3: 91 percent / H2 / 10percent Pd-C / ethanol 4: 62 percent / PPA / xylene; CHCl3 / 100 °C 5: NaBH4 / ethanol 6: 71 percent / 10percent H2SO4 / H2O / Heating 7: 91 percent / H2 / 10 percent Pd-C / ethanol View Scheme

1: 71 percent / (Et2AlH2)Na / toluene; tetrahydrofuran 2: 74 percent / Et3N / benzene 3: 84 percent / benzene / 1 h / Ambient temperature 4: 91 percent / H2 / 10percent Pd-C / ethanol 5: 62 percent / PPA / xylene; CHCl3 / 100 °C 6: NaBH4 / ethanol 7: 71 percent / 10percent H2SO4 / H2O / Heating 8: 91 percent / H2 / 10 percent Pd-C / ethanol View Scheme

1: 84 percent / benzene / 1 h / Ambient temperature 2: 91 percent / H2 / 10percent Pd-C / ethanol 3: 62 percent / PPA / xylene; CHCl3 / 100 °C 4: NaBH4 / ethanol 5: 71 percent / 10percent H2SO4 / H2O / Heating 6: 91 percent / H2 / 10 percent Pd-C / ethanol View Scheme

1: NaBH4 / ethanol 2: 71 percent / 10percent H2SO4 / H2O / Heating 3: 91 percent / H2 / 10 percent Pd-C / ethanol View Scheme

1: 62 percent / PPA / xylene; CHCl3 / 100 °C 2: NaBH4 / ethanol 3: 71 percent / 10percent H2SO4 / H2O / Heating 4: 91 percent / H2 / 10 percent Pd-C / ethanol View Scheme

1: 71 percent / 10percent H2SO4 / H2O / Heating 2: 91 percent / H2 / 10 percent Pd-C / ethanol View Scheme

1: 91 percent / H2 / 10percent Pd-C / ethanol 2: 62 percent / PPA / xylene; CHCl3 / 100 °C 3: NaBH4 / ethanol 4: 71 percent / 10percent H2SO4 / H2O / Heating 5: 91 percent / H2 / 10 percent Pd-C / ethanol View Scheme

1: Br2 / acetic acid; H2O 3: H2SO4 / Heating 4: LiAlH4 / diethyl ether 5: SOCl2 / pyridine; benzene 6: 73 percent / acetonitrile / 4 h / Heating 7: 30 percent / (Et2AlH2)Na / toluene; tetrahydrofuran / 4 h / Ambient temperature View Scheme