toluene-4-sulfonic acid 48 h; Ambient temperature;

4 A molecular sieve; toluene-4-sulfonic acid in chloroform 17 h; Heating;

potassium carbonate; toluene-4-sulfonic acid in acetone

in sodium hydrogencarbonate; N,N-dimethyl-formamide

1: 59 percent / Na (methal) / xylene / 2 h / 100 °C 2: 91 percent / H2O, 7 percent HCl 3: 45 percent / NaH / tetrahydrofuran / 12 h / Heating 4: 90 percent / H2 / ethanol / 4 h / 2280 Torr / Ambient temperature View Scheme

1: 63 percent / 1.) sodium / toluene / Heating; 1.) 20 h; 2.) 3 h 2: 95 percent / hydrochloric acid / H2O; tetrahydrofuran / 0.5 h / Heating 3: thionyl chloride / pyridine / 115 °C View Scheme

1: 100 percent / Et3N / CH2Cl2 / 6 h / Heating 2: 100 percent / sodium tetrakis(3,5-trifluoromethylphenyl)borate dihydrate / H2O / 24 h / 30 °C View Scheme

sodium hypochlorite; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; sodium hydrogencarbonate; potassium bromide in dichloromethane; water T=20°C; 0.583333 h; Inert atmosphere;

1: 1) NaH (80percent in paraffine oil) / 1) anh. THF, 30 min, r. t., 2) THF, 6 h, reflux 2: 88 percent / 0.2N H2SO4 / 16 h / Heating 3: 48 percent / NaH (80percent in paraffine oil) / tetrahydrofuran / 12 h / Heating 4: 97 percent / H2, Pd/C (10percent) / ethanol / 4 h / Ambient temperature View Scheme