1: 68 percent / H2 / 10percent Pd/C / ethanol / 5 h / 2068.6 Torr 2: 60 percent / decalin / 3 h / 160 °C 3: 50 percent / Ag2O, nitric acid / dioxane / 0.25 h / Ambient temperature View Scheme

With  hydrogen; palladium on activated charcoal in  ethanol P=2068.6 Torr; 5 h;   

Multi-step reaction with 2 steps 1: 2.) Zn/glacial acetic acid / 1.) 80 deg C, 8 h; 2.) 5 min2: 75 percent / NaOH / methanol; H2O / Ambient temperature