toluene-4-sulfonic acid in ethanol

in ethanol

toluene-4-sulfonic acid 17 h; Heating;

1: 85 percent / pyridine; ethanol / 22 h / Ambient temperature 2: 80 percent / KOH / methanol; H2O / 18 h / Heating 3: 86.2 percent / triethylamine / CH2Cl2 / 0.5 h / cooling 4: 90.6 g / dimethylformamide / 3 h / 70 °C 5: NaOH / methanol; H2O / 72 h / Heating 6: 63.3 percent / 2N HCl / acetone / 5 h / Heating 7: 87.3 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme

1: 85.9 percent / 25percent (i-Bu)2AlH / benzene; hexane / 1.5 h / 0 - 5 °C / 1) 0-5 deg C, 1.5h, 2) 15 min 2: 86.2 percent / triethylamine / CH2Cl2 / 0.5 h / cooling 3: 90.6 g / dimethylformamide / 3 h / 70 °C 4: NaOH / methanol; H2O / 72 h / Heating 5: 63.3 percent / 2N HCl / acetone / 5 h / Heating 6: 87.3 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme

1: 89 percent / p-toluenesulfonic acid / 8 h / Heating 2: CaCO3, Br2, sodium thiosulfate, LiBr, Li2CO3, p-toluenesulfonic acid 3: 84.1 percent / pyridine; ethanol / 22 h / Ambient temperature 4: 85.9 percent / 25percent (i-Bu)2AlH / benzene; hexane / 1.5 h / 0 - 5 °C / 1) 0-5 deg C, 1.5h, 2) 15 min 5: 86.2 percent / triethylamine / CH2Cl2 / 0.5 h / cooling 6: 90.6 g / dimethylformamide / 3 h / 70 °C 7: NaOH / methanol; H2O / 72 h / Heating 8: 63.3 percent / 2N HCl / acetone / 5 h / Heating 9: 87.3 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme

1: CaCO3, Br2, sodium thiosulfate, LiBr, Li2CO3, p-toluenesulfonic acid 2: 84.1 percent / pyridine; ethanol / 22 h / Ambient temperature 3: 85.9 percent / 25percent (i-Bu)2AlH / benzene; hexane / 1.5 h / 0 - 5 °C / 1) 0-5 deg C, 1.5h, 2) 15 min 4: 86.2 percent / triethylamine / CH2Cl2 / 0.5 h / cooling 5: 90.6 g / dimethylformamide / 3 h / 70 °C 6: NaOH / methanol; H2O / 72 h / Heating 7: 63.3 percent / 2N HCl / acetone / 5 h / Heating 8: 87.3 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme

1: 90.6 g / dimethylformamide / 3 h / 70 °C 2: NaOH / methanol; H2O / 72 h / Heating 3: 63.3 percent / 2N HCl / acetone / 5 h / Heating 4: 87.3 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme

1: 86.2 percent / triethylamine / CH2Cl2 / 0.5 h / cooling 2: 90.6 g / dimethylformamide / 3 h / 70 °C 3: NaOH / methanol; H2O / 72 h / Heating 4: 63.3 percent / 2N HCl / acetone / 5 h / Heating 5: 87.3 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme

1: 80 percent / KOH / methanol; H2O / 18 h / Heating 2: 86.2 percent / triethylamine / CH2Cl2 / 0.5 h / cooling 3: 90.6 g / dimethylformamide / 3 h / 70 °C 4: NaOH / methanol; H2O / 72 h / Heating 5: 63.3 percent / 2N HCl / acetone / 5 h / Heating 6: 87.3 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme