pyridine; thionyl chloride in benzene

sulfuric acid; sulfur trioxide T=5°C;

sulfuryl dichloride; dibenzoyl peroxide

hydrogenchloride; N-benzyl-N,N,N-triethylammonium chloride; potassium acetate 1) DMSO, 60 deg C, 4 h; 2) EtOH/H2O, reflux, 7 h; Yield given. Multistep reaction;

1: 1) CH3CO2K, triethylbenzylammonium chloride; 2) HCl / 1) DMSO, 60 deg C, 4 h; 2) EtOH/H2O, reflux, 7 h 2: 98 percent / K2Cr2O7/H2SO4 / Triethylbenzylammonium chloride / CH2Cl2; H2O / 4 h / Ambient temperature 3: 75 percent / NaOH / hexamethylphosphoric acid triamide; H2O / 5.5 h / 100 °C 4: Mg / 1) THF, reflux, 1 h; 2) THF, reflux. 4.5 h 5: 0.62 g / NaH / dimethylformamide / 14 h / 70 °C View Scheme

in dimethyl sulfoxide T=40 - 50°C; 5 h; Yield given;

1: 1) CH3CO2K, triethylbenzylammonium chloride; 2) HCl / 1) DMSO, 60 deg C, 4 h; 2) EtOH/H2O, reflux, 7 h 2: 98 percent / K2Cr2O7/H2SO4 / Triethylbenzylammonium chloride / CH2Cl2; H2O / 4 h / Ambient temperature View Scheme

1: dimethylsulfoxide / 5 h / 40 - 50 °C 2: 25 percent NaOH / ethanol / Heating View Scheme

sodium hydride in N,N-dimethyl-formamide 1.) room temp., 10 min, 2.) 90 deg C;

1: 80 percent / 1.) NaH / dimethylformamide / 1.) room temp., 10 min, 2.) 90 deg C 2: KMnO4 / acetone; H2O / 16 h / Ambient temperature View Scheme