hydrogen; palladium on activated charcoal in ethanol; ethyl acetate T=20°C;

1: 92 percent / benzene / 24 h / 25 °C 2: 77 percent / LiAlH4 / tetrahydrofuran / 2 h / 0 °C 3: 80 percent / H2 / 10 percent Pd/C / ethanol; ethyl acetate / 20 °C View Scheme

1: 96 percent / K2CO3 / acetone / 5 h / 50 °C 2: 91 percent / LiAlH4 3: 90 percent / C5H5*CrO3*HCl / CH2Cl2 / 8 h / 0 °C 4: 92 percent / benzene / 24 h / 25 °C 5: 77 percent / LiAlH4 / tetrahydrofuran / 2 h / 0 °C 6: 80 percent / H2 / 10 percent Pd/C / ethanol; ethyl acetate / 20 °C View Scheme

1: 91 percent / LiAlH4 2: 90 percent / C5H5*CrO3*HCl / CH2Cl2 / 8 h / 0 °C 3: 92 percent / benzene / 24 h / 25 °C 4: 77 percent / LiAlH4 / tetrahydrofuran / 2 h / 0 °C 5: 80 percent / H2 / 10 percent Pd/C / ethanol; ethyl acetate / 20 °C View Scheme

1: 90 percent / H2SO4 2: 96 percent / K2CO3 / acetone / 5 h / 50 °C 3: 91 percent / LiAlH4 4: 90 percent / C5H5*CrO3*HCl / CH2Cl2 / 8 h / 0 °C 5: 92 percent / benzene / 24 h / 25 °C 6: 77 percent / LiAlH4 / tetrahydrofuran / 2 h / 0 °C 7: 80 percent / H2 / 10 percent Pd/C / ethanol; ethyl acetate / 20 °C View Scheme

1: 90 percent / C5H5*CrO3*HCl / CH2Cl2 / 8 h / 0 °C 2: 92 percent / benzene / 24 h / 25 °C 3: 77 percent / LiAlH4 / tetrahydrofuran / 2 h / 0 °C 4: 80 percent / H2 / 10 percent Pd/C / ethanol; ethyl acetate / 20 °C View Scheme

1: 77 percent / LiAlH4 / tetrahydrofuran / 2 h / 0 °C 2: 80 percent / H2 / 10 percent Pd/C / ethanol; ethyl acetate / 20 °C View Scheme