acetic acid T=70°C; 0.5 h;

1: 94 percent / p-toluenesulfonic acid / benzene / 72 h / Heating 2: 1. sodium; 2. potassium iodide, cupric oxide / 2. 90 degC, 3d 3: 76 percent / p-toluenesulfonic acid / acetone / 18 h / Heating 4: 35 percent / hydroxylamine hydrochloride / triethylamine / 1 h / Heating 5: 74 percent / p-toluenesulfonyl chloride, sodium hydroxide / acetone; H2O / 3 h 6: 83 percent / 80percent aq. acetic acid / 0.5 h / 70 °C View Scheme

1: 1. sodium; 2. potassium iodide, cupric oxide / 2. 90 degC, 3d 2: 76 percent / p-toluenesulfonic acid / acetone / 18 h / Heating 3: 35 percent / hydroxylamine hydrochloride / triethylamine / 1 h / Heating 4: 74 percent / p-toluenesulfonyl chloride, sodium hydroxide / acetone; H2O / 3 h 5: 83 percent / 80percent aq. acetic acid / 0.5 h / 70 °C View Scheme

1: 35 percent / hydroxylamine hydrochloride / triethylamine / 1 h / Heating 2: 74 percent / p-toluenesulfonyl chloride, sodium hydroxide / acetone; H2O / 3 h 3: 83 percent / 80percent aq. acetic acid / 0.5 h / 70 °C View Scheme

1: 76 percent / p-toluenesulfonic acid / acetone / 18 h / Heating 2: 35 percent / hydroxylamine hydrochloride / triethylamine / 1 h / Heating 3: 74 percent / p-toluenesulfonyl chloride, sodium hydroxide / acetone; H2O / 3 h 4: 83 percent / 80percent aq. acetic acid / 0.5 h / 70 °C View Scheme

1: 74 percent / p-toluenesulfonyl chloride, sodium hydroxide / acetone; H2O / 3 h 2: 83 percent / 80percent aq. acetic acid / 0.5 h / 70 °C View Scheme

sodium hydroxide; p-toluenesulfonyl chloride 1. pyridine, r.t., 1d; 2. 1.5N sulfuric acid, ice-bath; 3. DMSO, r.t., 1h; Yield given. Multistep reaction;