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

1: 85.3 percent / p-Toluenesulfonic acid / 18 h / Heating 2: 83.9 percent / CrO3, pyridine / CH2Cl2 / 0.33 h 3: 81.4 percent / NaH, Me2SO / 30 h / Ambient temperature 4: 80 percent / H2 / Pd/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature View Scheme

1: 83.9 percent / CrO3, pyridine / CH2Cl2 / 0.33 h 2: 81.4 percent / NaH, Me2SO / 30 h / Ambient temperature 3: 80 percent / H2 / Pd/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature View Scheme

1: 89.8 percent / benzene / 24 h / Heating 2: 81.4 percent / NaH, Me2SO / 30 h / Ambient temperature 3: 80 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: 81.4 percent / NaH, Me2SO / 30 h / Ambient temperature 4: 80 percent / H2 / Pd/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature View Scheme

1: 81.4 percent / NaH, Me2SO / 30 h / Ambient temperature 2: 80 percent / H2 / Pd/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature View Scheme

1: 81.4 percent / NaH, Me2SO / 30 h / Ambient temperature 2: 80 percent / H2 / Pd/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature View Scheme