tri-n-butyl-tin hydride; [Mn(pic)3] in N,N-dimethyl-formamide T=0°C;

lead(IV) acetate; benzene

1: H2SO4 / Heating 2: PCC / CH2Cl2 / Ambient temperature View Scheme

palladium(II)-hydroxide-barium sulfate-catalyst; xylene T=130 - 140°C; Hydrogenation;

1: 28 percent / lithium chloride, copper(II)chloride / tetrahydrofuran / -10 °C 2: 80 percent / benzoic acid / H2O / 1.25 h / Heating View Scheme

oxygen in pentane T=20°C; 0.25 h; UV-irradiation; Reactivity; Time;

1: 71 percent / tetrahydrofuran / 1 h / 0 °C 2: 91 percent / potassium hydroxide / aq. ethanol / 2.5 h / Ambient temperature 3: 60 percent / pyridine / Ambient temperature 4: thionyl chloride / diethyl ether / 4 h / Ambient temperature 5: 84 percent / pyridine / CH2Cl2 / 2 h / Heating 6: 1.) sodium hydride / 2.) tetrakis(triphenylphosphine)palladium(0) / 1.) THF, room temperature, 30 min, 2.) reflux, 2.5 h 7: 76 percent / tetramethylammonium acetate / hexamethylphosphoric acid triamide / 6 h / 90 - 95 °C 8: disodium hydrogen phosphate, 6percent sodium amalgam / tetrahydrofuran; ethanol / 2.5 h / -20 °C 9: 98 percent / hydrogen / 5percent palladium on barium carbonate / ethanol / 2 h / 1520 Torr / Ambient temperature View Scheme

potassium tert-butylate; triphenylphosphine in toluene T=-20°C;

ethanol; sulfuric acid