ethylene glycol T=200°C; P=2 Torr; Erhitzen des Reaktionsprodukts mit wenig Zinn(II)-chlorid-dihydrat unter 1 Torr auf 270grad;

toluene-4-sulfonic acid in benzene 10 h;

1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating View Scheme

lithium aluminium tetrahydride in diethyl ether 3.5 h; Ambient temperature;

1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature View Scheme

1: 98 percent / LiAlH4 / diethyl ether / 3.5 h / Ambient temperature 2: 72 percent / 48percent HBr / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 91 percent / xylene; tetrahydrofuran; hexamethylphosphoric acid triamide / 36 h / Ambient temperature 5: 1.) 1.63N butyllithium / 1.) hexane, THF, -50 deg C, 30 min; 0 deg C, 30 min, 2.) hexane, THF, HMPA, -50 deg C, 30 min; 0 deg C, 2 h 6: 99 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h / Ambient temperature 7: 92 percent / 1,3-propanediamine, Li, potassium tert-butoxide / 2 h / Ambient temperature View Scheme