toluene-4-sulfonic acid in benzene Heating;

1: 1.) NaH / 1.)a) THF, RT, 10 min, b) reflux, 15 min, 2.) THF, reflux, 1.5 h 2: 91 percent / LAH / tetrahydrofuran / 2 h / Heating 3: 46 percent / p-toluenesulfonic acid / benzene / Heating View Scheme

1: potassium carbonate / dimethylformamide / 70 °C 2: aq.HCl / benzene / 24 h / Heating 3: 1.) NaH / 1.)a) THF, RT, 10 min, b) reflux, 15 min, 2.) THF, reflux, 1.5 h 4: 91 percent / LAH / tetrahydrofuran / 2 h / Heating 5: 46 percent / p-toluenesulfonic acid / benzene / Heating View Scheme

1: 91 percent / LAH / tetrahydrofuran / 2 h / Heating 2: 46 percent / p-toluenesulfonic acid / benzene / Heating View Scheme

1: potassium carbonate / dimethylformamide / 70 °C 2: aq.HCl / benzene / 24 h / Heating 3: 1.) NaH / 1.)a) THF, RT, 10 min, b) reflux, 15 min, 2.) THF, reflux, 1.5 h 4: 91 percent / LAH / tetrahydrofuran / 2 h / Heating 5: 46 percent / p-toluenesulfonic acid / benzene / Heating View Scheme

1: aq.HCl / benzene / 24 h / Heating 2: 1.) NaH / 1.)a) THF, RT, 10 min, b) reflux, 15 min, 2.) THF, reflux, 1.5 h 3: 91 percent / LAH / tetrahydrofuran / 2 h / Heating 4: 46 percent / p-toluenesulfonic acid / benzene / Heating View Scheme