1: 80 percent / p-toluenesulfonic acid / ethanol / 45 °C 2: 75 percent / H2, quinoline / Lindlar catalyst / hexane / 1.5 h / 25 °C / 760 Torr 3: 90 percent / LiOH / tetrahydrofuran; H2O / 25 °C View Scheme

With  toluene-4-sulfonic acid in  ethanol T=45°C;   

Multi-step reaction with 3 steps 1: pyridinium chlorochromate / CH2Cl2 / 25 °C2: sodium bis<trimethylsilyl>amide / 1,2-dimethoxy-ethane / 0 - 25 °C3: 88 percent / n-propylamine / tetrakis<triphenylphosphine>palladium, copper(I) iodide / benzene / 25 °C  

Multi-step reaction with 2 steps 1: tetra-n-butylammonium fluoride / tetrahydrofuran / 25 °C2: 88 percent / n-propylamine / tetrakis<triphenylphosphine>palladium, copper(I) iodide / benzene / 25 °C  

Multi-step reaction with 3 steps 1: H2 / Lindlar catalyst / hexane / 25 °C2: tetra-n-butylammonium fluoride / tetrahydrofuran / 25 °C3: 88 percent / n-propylamine / tetrakis<triphenylphosphine>palladium, copper(I) iodide / benzene / 25 °C