1: 95 percent / H2 / 10 percent Pd/C / ethanol / 3 h / 2280 Torr 2: O3 / CH2Cl2; methanol / 1 h 3: methanol / 0.67 h / Heating 4: <<(C6H5)3P>Cu>BH4 / CHCl3 / 4 h / Heating View Scheme

1: 95 percent / H2 / 10 percent Pd/C / ethanol / 3 h / 2280 Torr 2: O3 / CH2Cl2; methanol / 1 h View Scheme

With  hydrogen; palladium on activated charcoal in  ethanol P=2280 Torr; 3 h;   

With  3-chloro-benzenecarboperoxoic acid in  chloroform T=0°C; 0.5 h;