hydrogen; palladium on activated charcoal in ethyl acetate P=760 Torr; 4 h; Ambient temperature;

1: 96 percent / CrO3, pyridine / CH2Cl2 / 0.33 h 2: 89.7 percent / NaH, Me2SO / 24 h / Ambient temperature 3: 79.6 percent / H2 / Pd/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature View Scheme

1: 89.7 percent / NaH, Me2SO / 24 h / Ambient temperature 2: 79.6 percent / H2 / Pd/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature View Scheme

1: 89.8 percent / benzene / 24 h / Heating 2: 89.7 percent / NaH, Me2SO / 24 h / Ambient temperature 3: 79.6 percent / H2 / Pd/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature View Scheme

1: 84.1 percent / Br2, Triphenylphosphine / dimethylformamide / 1.25 h 2: 89.8 percent / benzene / 24 h / Heating 3: 89.7 percent / NaH, Me2SO / 24 h / Ambient temperature 4: 79.6 percent / H2 / Pd/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature View Scheme

1: 47.5 percent / H2SO4 conc. / 18 h / Heating 2: 96 percent / CrO3, pyridine / CH2Cl2 / 0.33 h 3: 89.7 percent / NaH, Me2SO / 24 h / Ambient temperature 4: 79.6 percent / H2 / Pd/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature View Scheme

1: 79.1 percent / n-BuLi / tetrahydrofuran; hexane / 1) -78 deg C, 10 min 2) r.t., 90 min 2: 47.5 percent / H2SO4 conc. / 18 h / Heating 3: 96 percent / CrO3, pyridine / CH2Cl2 / 0.33 h 4: 89.7 percent / NaH, Me2SO / 24 h / Ambient temperature 5: 79.6 percent / H2 / Pd/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature View Scheme

1: 89.7 percent / NaH, Me2SO / 24 h / Ambient temperature 2: 79.6 percent / H2 / Pd/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature View Scheme