1: 84 percent / H2 / 5percent Pd/C / tetrahydrofuran / 50 - 60 °C / 2585.7 Torr 2: 1.) NaH / 1.) DMF, 2.) DMF, 50-60 deg, 6 h 3: water, HCl View Scheme

hydrogen; nickel in methanol P=3361.46 Torr; 5 h;

1: 84 percent / H2 / 5percent Pd/C / tetrahydrofuran / 50 - 60 °C / 2585.7 Torr 2: NaOH / H2O / 12 h / Ambient temperature 3: 48 h / Heating View Scheme

1: 86 percent / Raney Nickel; H2 / methanol / 5 h / 3361.46 Torr 2: 95 percent / potassium hydroxide; tetrabutylammonium bromide / tetrahydrofuran / 6 h / 20 °C 3: 75 percent / meta-chloroperbenzoic acid / CH2Cl2 / 24 h / 20 °C View Scheme