hydrogen; sodium acetate; palladium on activated charcoal in methanol; benzene T=40°C;

1: 82 percent / Ag2O / CHCl3 / 40 - 50 °C 2: 1) Zn; 2) NaOH / 1) CHCl3, glacial acetic acid; 2) dioxane, H2O, 12 h 3: 90 percent / H2 / 10 percent Pd/C / benzene; methanol / Ambient temperature 4: 86 percent / FeCl3*6H2O / acetonitrile 5: 70 percent / 4-(dimethylamino)pyridine, triethylamine / 15 h / Ambient temperature 6: 16 percent / H2, sodium acetate / 10 percent Pd/C / benzene; methanol / 40 °C View Scheme

1: 1) Zn; 2) NaOH / 1) CHCl3, glacial acetic acid; 2) dioxane, H2O, 12 h 2: 90 percent / H2 / 10 percent Pd/C / benzene; methanol / Ambient temperature 3: 86 percent / FeCl3*6H2O / acetonitrile 4: 70 percent / 4-(dimethylamino)pyridine, triethylamine / 15 h / Ambient temperature 5: 16 percent / H2, sodium acetate / 10 percent Pd/C / benzene; methanol / 40 °C View Scheme

1: 90 percent / H2 / 10 percent Pd/C / benzene; methanol / Ambient temperature 2: 86 percent / FeCl3*6H2O / acetonitrile 3: 70 percent / 4-(dimethylamino)pyridine, triethylamine / 15 h / Ambient temperature 4: 16 percent / H2, sodium acetate / 10 percent Pd/C / benzene; methanol / 40 °C View Scheme

1: 86 percent / FeCl3*6H2O / acetonitrile 2: 70 percent / 4-(dimethylamino)pyridine, triethylamine / 15 h / Ambient temperature 3: 16 percent / H2, sodium acetate / 10 percent Pd/C / benzene; methanol / 40 °C View Scheme

1: 70 percent / 4-(dimethylamino)pyridine, triethylamine / 15 h / Ambient temperature 2: 16 percent / H2, sodium acetate / 10 percent Pd/C / benzene; methanol / 40 °C View Scheme