toluene-4-sulfonic acid in ethylene glycol; benzene

toluene-4-sulfonic acid; benzene Erwaermen des Reaktionsprodukts mit methanol. Natronlauge;

1: 4-hydroxy-cyclohexanone With lithium hexamethyldisilazane in tetrahydrofuran 2: methoxycarbonyl cyanide in tetrahydrofuran T=-78 - 20°C;

1: 99 percent / imidazole 2: ZnI2 / CH2Cl2 / 5 h / 20 °C 3: 81 percent / aq. HCl / Heating 4: 53 percent / DEAD; Ph3P / tetrahydrofuran View Scheme

1: 94 percent / p-toluenesulfonic acid monohydrate / CH2Cl2 / 1.5 h / ice-bath 2: 78 percent / diethyl ether / 1 h / Ambient temperature 3: 61 percent / pyridinium p-toluenesulfonate / ethanol / 4 h / 60 - 70 °C 4: 88 percent / pyridinium chlorochromate (PCC), NaOAc / CH2Cl2 / 8 h / Ambient temperature View Scheme

pyridine T=20°C;

1: 94 percent / p-toluenesulfonic acid monohydrate / CH2Cl2 / 1.5 h / ice-bath 2: 78 percent / diethyl ether / 1 h / Ambient temperature 3: 61 percent / pyridinium p-toluenesulfonate / ethanol / 4 h / 60 - 70 °C 4: 88 percent / pyridinium chlorochromate (PCC), NaOAc / CH2Cl2 / 8 h / Ambient temperature 5: 84 percent / dimethylformamide / 80 °C 6: 1) lithium diisopropylamide / 1) THF, -60 deg C, 20 min, 2) -60 to -5 deg C 7: 1) lithium diisopropylamide / 1) THF, -70 deg C, 15 min, 2) -70 deg C, 1 h 8: 30 percent aq. acetic acid / tetrahydrofuran / 3 h / Ambient temperature 9: 71 percent / triethylamine, 4-dimethylaminopyridine / 48 h / Ambient temperature 10: 40 percent / triethylamine, 4-dimethylaminopyridine / 7 h / ice-NaCl bath 11: 70 percent / aq. acetic acid / tetrahydrofuran / 4 h / Ambient temperature View Scheme

toluene-4-sulfonic acid in benzene 4.6 h; Heating;

1: p-toluenesulfonic acid / benzene / 4.6 h / Heating 2: CrO3, 3,5-dimethylpyrazole / CH2Cl2 / 0.17 h 3: 92 percent / H2O; methanol / 48 h / Ambient temperature 4: 1.) Mg / 1.) THF, 2.) THF, reflux, 24 h 5: etheral HCl View Scheme

1: 54 percent / p-toluenesulfonic acid / benzene / 4.6 h / Heating 2: 88 percent / CrO3, 3,5-dimethylpyrazole / CH2Cl2 / 0.17 h 3: 84 percent / H2O; methanol / 48 h / Ambient temperature 4: 1.) Mg / 1.) THF, 2.) THF, reflux, 24 h 5: etheral HCl View Scheme