hydrogen; palladium on activated charcoal P=2585.7 Torr; 20 h;

hydrogen; palladium dihydroxide in ethanol P=2585.7 Torr; 2 h;

1: 69 percent / dimethylformamide / 3 h / 90 °C 2: p-toluenesulfonic acid / acetonitrile; H2O / 5 h / Heating View Scheme

1: 69 percent / dimethylformamide / 3 h / 90 °C 2: p-toluenesulfonic acid / acetonitrile; H2O / 5 h / Heating 3: HCO2H; aq. H2O2 / 0 - 5 °C View Scheme

1: 88 percent / potassium, EtOH / toluene / 2 h / Ambient temperature 2: 62 percent / H2 / 10percent Pd/C / CH2Cl2 / 2 h / 1551.4 Torr 3: 77 percent / p-toluenesulfonic acid monohydrate / acetonitrile; H2O / 5 h / Heating View Scheme

1: 1.) potassium, ethanol / 1.) room temperature, 15 min, 2.) toluene, room temperature, 2 h 2: 62 percent / H2 / 10percent Pd/C / CH2Cl2 / 2 h / 1551.4 Torr 3: 77 percent / p-toluenesulfonic acid monohydrate / acetonitrile; H2O / 5 h / Heating 4: 89 percent / 33percent H2O2, formic acid / H2O / 4 °C View Scheme

With  toluene-4-sulfonic acid in  ethylene glycol; toluene Show Experimental Procedure  

Multi-step reaction with 2 steps 1: dimethylformamide / 4 h / 90 °C2: H2 / 1) 5percent Pd/BaSO4 2) 10percent Pd/C / 1) 2) EtOH, atmospheric pressure