1: 76 percent / 10 percent KOH / tetrahydrofuran / 2 h / Heating 2: 1.74 g / H2, 5 percent palladium/charcoal / ethyl acetate / 1 h 3: 88 percent / 48 percent HBr / acetic acid / 4 h / 100 °C 4: 90 percent / Jones reagent / acetone View Scheme

1: 76 percent / 10 percent KOH / tetrahydrofuran / 2 h / Heating 2: 1.74 g / H2, 5 percent palladium/charcoal / ethyl acetate / 1 h 3: 88 percent / 48 percent HBr / acetic acid / 4 h / 100 °C View Scheme