toluene-4-sulfonic acid in benzene diethyl ether; ethanol; benzene

toluene-4-sulfonic acid 17 h; Heating;

1: LiBr, Li2CO3 / DMF, reflux, 0.5h 2: 95.8 percent / pyridine; ethanol / 22 h / Ambient temperature 3: 84.6 percent / 25percent (i-Bu)2AlH / benzene; hexane / 1.5 h / 0 - 5 °C 4: 77.9 percent / triethylamine / CH2Cl2 / 0.5 h 5: 57percent NaH / 1,2-dimethoxy-ethane / 18 h / Heating 6: 64.2 percent / KOH / H2O; methanol / 18 h / Heating 7: 84 percent / various solvent(s) / Heating 8: 90 percent / 2N HCl / acetone / 5 h / Heating 9: 94.9 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme

1: 56 percent 2: p-toluenesulfonic acid / Heating 3: 1) CaCO3, Br2, 2) Li2CO3, / 1) CCl4, water, 0-5 deg C, 30 min, 2) DMF, 30 min, reflux 4: 95.8 percent / pyridine; ethanol / 22 h / Ambient temperature 5: 84.6 percent / 25percent (i-Bu)2AlH / benzene; hexane / 1.5 h / 0 - 5 °C 6: 77.9 percent / triethylamine / CH2Cl2 / 0.5 h 7: 57percent NaH / 1,2-dimethoxy-ethane / 18 h / Heating 8: 64.2 percent / KOH / H2O; methanol / 18 h / Heating 9: 84 percent / various solvent(s) / Heating 10: 90 percent / 2N HCl / acetone / 5 h / Heating 11: 94.9 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme

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: 1) 57percent NaH / 1) 1h, DME; 2) DME, 16h, reflux 5: KOH / methanol; H2O / 18 h / Heating 6: various solvent(s) / Heating 7: 2N HCl / acetone / 5 h / Heating 8: 87 percent / p-toluenesulfonic acid / 17 h / Heating 9: 95.8 percent / pyridine; ethanol / 22 h / Ambient temperature 10: 84.6 percent / 25percent (i-Bu)2AlH / benzene; hexane / 1.5 h / 0 - 5 °C 11: 77.9 percent / triethylamine / CH2Cl2 / 0.5 h 12: 57percent NaH / 1,2-dimethoxy-ethane / 18 h / Heating 13: 64.2 percent / KOH / H2O; methanol / 18 h / Heating 14: 84 percent / various solvent(s) / Heating 15: 90 percent / 2N HCl / acetone / 5 h / Heating 16: 94.9 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: 1) 57percent NaH / 1) 1h, DME; 2) DME, 16h, reflux 4: KOH / methanol; H2O / 18 h / Heating 5: various solvent(s) / Heating 6: 2N HCl / acetone / 5 h / Heating 7: 87 percent / p-toluenesulfonic acid / 17 h / Heating 8: 95.8 percent / pyridine; ethanol / 22 h / Ambient temperature 9: 84.6 percent / 25percent (i-Bu)2AlH / benzene; hexane / 1.5 h / 0 - 5 °C 10: 77.9 percent / triethylamine / CH2Cl2 / 0.5 h 11: 57percent NaH / 1,2-dimethoxy-ethane / 18 h / Heating 12: 64.2 percent / KOH / H2O; methanol / 18 h / Heating 13: 84 percent / various solvent(s) / Heating 14: 90 percent / 2N HCl / acetone / 5 h / Heating 15: 94.9 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme

1: KOH / methanol; H2O / 18 h / Heating 2: various solvent(s) / Heating 3: 2N HCl / acetone / 5 h / Heating 4: 87 percent / p-toluenesulfonic acid / 17 h / Heating 5: 95.8 percent / pyridine; ethanol / 22 h / Ambient temperature 6: 84.6 percent / 25percent (i-Bu)2AlH / benzene; hexane / 1.5 h / 0 - 5 °C 7: 77.9 percent / triethylamine / CH2Cl2 / 0.5 h 8: 57percent NaH / 1,2-dimethoxy-ethane / 18 h / Heating 9: 64.2 percent / KOH / H2O; methanol / 18 h / Heating 10: 84 percent / various solvent(s) / Heating 11: 90 percent / 2N HCl / acetone / 5 h / Heating 12: 94.9 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: 1) 57percent NaH / 1) 1h, DME; 2) DME, 16h, reflux 7: KOH / methanol; H2O / 18 h / Heating 8: various solvent(s) / Heating 9: 2N HCl / acetone / 5 h / Heating 10: 87 percent / p-toluenesulfonic acid / 17 h / Heating 11: 95.8 percent / pyridine; ethanol / 22 h / Ambient temperature 12: 84.6 percent / 25percent (i-Bu)2AlH / benzene; hexane / 1.5 h / 0 - 5 °C 13: 77.9 percent / triethylamine / CH2Cl2 / 0.5 h 14: 57percent NaH / 1,2-dimethoxy-ethane / 18 h / Heating 15: 64.2 percent / KOH / H2O; methanol / 18 h / Heating 16: 84 percent / various solvent(s) / Heating 17: 90 percent / 2N HCl / acetone / 5 h / Heating 18: 94.9 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme

1: 2N HCl / acetone / 5 h / Heating 2: 87 percent / p-toluenesulfonic acid / 17 h / Heating 3: 95.8 percent / pyridine; ethanol / 22 h / Ambient temperature 4: 84.6 percent / 25percent (i-Bu)2AlH / benzene; hexane / 1.5 h / 0 - 5 °C 5: 77.9 percent / triethylamine / CH2Cl2 / 0.5 h 6: 57percent NaH / 1,2-dimethoxy-ethane / 18 h / Heating 7: 64.2 percent / KOH / H2O; methanol / 18 h / Heating 8: 84 percent / various solvent(s) / Heating 9: 90 percent / 2N HCl / acetone / 5 h / Heating 10: 94.9 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme

1: 95.8 percent / pyridine; ethanol / 22 h / Ambient temperature 2: 84.6 percent / 25percent (i-Bu)2AlH / benzene; hexane / 1.5 h / 0 - 5 °C 3: 77.9 percent / triethylamine / CH2Cl2 / 0.5 h 4: 57percent NaH / 1,2-dimethoxy-ethane / 18 h / Heating 5: 64.2 percent / KOH / H2O; methanol / 18 h / Heating 6: 84 percent / various solvent(s) / Heating 7: 90 percent / 2N HCl / acetone / 5 h / Heating 8: 94.9 percent / p-toluenesulfonic acid / 17 h / Heating View Scheme