toluene-4-sulfonic acid in benzene 2 h; Heating;

1: 99 percent / H2 / Raney nickel (W-7) / methanol / 4 h / 130 °C / 95616.1 Torr 2: 8N Jones chromic acid reagent / acetone / 1 h / Ambient temperature 3: p-toluenesulfonic acid monohydrate / benzene / 20 h / Heating; azeotropic removal of water 4: p-toluenesulfonic acid monohydrate, H2O / acetone / 2 h / Heating View Scheme

1: 81 percent / H2 / Raney-Nickel / ethanol / 150 °C / 114000 Torr 2: 70 percent / pyridiniumchlorochromate / CH2Cl2 / 2 h / 20 °C 3: 85 percent / p-toluen sulfonic acid / benzene / 16 h / Heating 4: 71 percent / 15percent H2SO4 / CH2Cl2 / 4 h / Ambient temperature View Scheme

2: 81 percent / H2 / Raney-Nickel / ethanol / 150 °C / 114000 Torr 3: 70 percent / pyridiniumchlorochromate / CH2Cl2 / 2 h / 20 °C 4: 85 percent / p-toluen sulfonic acid / benzene / 16 h / Heating 5: 71 percent / 15percent H2SO4 / CH2Cl2 / 4 h / Ambient temperature View Scheme