hydrogen; palladium/alumina in methanol 4 h;

1: 1.) sodium tert-pentanoxide / benzene / 1.) 2 h, 2.) 12 h 2: H2 / 5percent Pd/Al2O3 / methanol / 4 h View Scheme

1: 1.) Et2O, -10 deg C, 1 h 2: 46 percent / LiAlH4 / dioxane / 17 h / Heating 3: 95 percent / H2 / 5percent Pd/Al2O3 / methanol / 5 h 4: 1.) sodium tert-pentanoxide / benzene / 1.) 2 h, 2.) 12 h 5: H2 / 5percent Pd/Al2O3 / methanol / 4 h View Scheme

1: 94 percent / NaOEt / ethanol / 8 h / Heating 2: 74 percent / 2.5 h / 120 °C / 10 - 20 Torr 3: 1.) Et2O, -10 deg C, 1 h 4: 46 percent / LiAlH4 / dioxane / 17 h / Heating 5: 95 percent / H2 / 5percent Pd/Al2O3 / methanol / 5 h 6: 1.) sodium tert-pentanoxide / benzene / 1.) 2 h, 2.) 12 h 7: H2 / 5percent Pd/Al2O3 / methanol / 4 h View Scheme

1: 95 percent / H2 / 5percent Pd/Al2O3 / methanol / 5 h 2: 1.) sodium tert-pentanoxide / benzene / 1.) 2 h, 2.) 12 h 3: H2 / 5percent Pd/Al2O3 / methanol / 4 h View Scheme

1: 74 percent / 2.5 h / 120 °C / 10 - 20 Torr 2: 1.) Et2O, -10 deg C, 1 h 3: 46 percent / LiAlH4 / dioxane / 17 h / Heating 4: 95 percent / H2 / 5percent Pd/Al2O3 / methanol / 5 h 5: 1.) sodium tert-pentanoxide / benzene / 1.) 2 h, 2.) 12 h 6: H2 / 5percent Pd/Al2O3 / methanol / 4 h View Scheme

1: 46 percent / LiAlH4 / dioxane / 17 h / Heating 2: 95 percent / H2 / 5percent Pd/Al2O3 / methanol / 5 h 3: 1.) sodium tert-pentanoxide / benzene / 1.) 2 h, 2.) 12 h 4: H2 / 5percent Pd/Al2O3 / methanol / 4 h View Scheme