1: 88 percent / n-propylamine / tetrakis<triphenylphosphine>palladium, copper(I) iodide / benzene / 25 °C 2: 80 percent / p-toluenesulfonic acid / ethanol / 45 °C 3: 75 percent / H2, quinoline / Lindlar catalyst / hexane / 1.5 h / 25 °C / 760 Torr 4: 90 percent / LiOH / tetrahydrofuran; H2O / 25 °C View Scheme

dicobalt octacarbonyl 1) light petroleum, r.t., 2 h, 2) toluene, 160 deg C, 50 atm, 3 h; Yield given. Multistep reaction;