lithium aluminium tetrahydride in diethyl ether T=0 - 20°C; 2 h;

1: 96 percent / hydrogen / 5percent palladium on charcoal / ethanol / 6 h / 760 Torr 2: 85 percent / lithium aluminium hydride / tetrahydrofuran / 0.5 h 3: 57 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / other reagent 4: 1.) n-butyl-lithium, TMEDA 2.) n-butyl-lithium / 1.) hexane, THF, 0 deg C, 15 min 2.) 30 min, hexane, THF 5: 23 percent / toluene-p-sulphonic acid / benzene / 0.02 h View Scheme

1: lithium aluminium tetrahydride / diethyl ether / 0 - 20 °C 2: diethylzinc / hexane; dichloromethane / 12 h / -20 °C / Inert atmosphere 3: pyridine; carbon tetrabromide; triphenylphosphine / dichloromethane / 1 h / 20 °C 4: 2,2'-azo-bisisobutyronitrile / benzene / 12 h / Inert atmosphere; Reflux View Scheme

1: 98 percent / NaOH / methanol; H2O / 8 h / Heating 2: 1.) aq. sodium hydroxide 2.) oxalyl chloride, pyridine / 1.) 95percent ethanol 2.) benzene, room temp., 3 h 3: 1.) diisopropylamide, n-butyllithium / 1.) THF, -78 deg C, 1 h 2.) THF, -78 deg C, 4 h 4: NaOH / H2O; methanol / 3 h / Heating 5: 20percent HCl / 40 °C 6: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 0.5 h 7: 1.) cupric acetate, pyridine, lead tetraacetate 2.) p-toluenesulfonic acid / 1.) benzene, room temp., 2 h, then 80 deg C, 1 h 2.) benzene, reflux, 3 h View Scheme