1: 98 percent / hydrogen / Lindlar catalyst / benzene / Ambient temperature 2: 90 percent / 90percent aqueous CF3COOH / 3 h / 0 °C 3: 65 percent / lead tetraacetate / benzene / 1 h / Ambient temperature 4: 50 percent / benzene / 4 h / Heating 5: NaH / 1.) benzene, RT, 1 h, 2.) benzene, RT, 4 h 6: 80 percent / potassium carbonate / ethanol / 22 h / 45 °C 7: 85 percent / dimethylformamide / 22 h / 65 °C 8: 100 percent / aluminum hydride / tetrahydrofuran / 2.5 h / 0 °C 9: 90 percent / CBr4, ethylenebis(diphenylphosphine) / CH2Cl2 / 2.5 h / -35 °C 10: 153 mg / acetonitrile / 1.5 h / 20 °C 11: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -100 deg C, 2 min, 2.) THF, hexane, from -100 deg C to RT 12: 61 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 15 h / Ambient temperature 13: potassium carbonate / methanol; H2O / 7.5 h / Ambient temperature 14: AcOH / H2O View Scheme