1: 90 percent / HCl / dioxane; H2O / 1 h / 100 °C 2: 98.5 percent / diisobutylaluminum hydride / toluene / 1.) 15 min. -10 deg C. 2.) 2 h, room temp. 3: 89 percent / 63percent HBr / H2O / 8 h / 80 - 90 °C 4: 91 percent / dibenzo-18-crown-6 / acetonitrile / 1.) 50 deg C, 2.) 3 h, 80 deg C 5: 82.1 percent / NaOH / dimethylsulfoxide; H2O / 3 h / 120 °C View Scheme

1: 90 percent / HCl / dioxane; H2O / 1 h / 100 °C 2: 98.5 percent / diisobutylaluminum hydride / toluene / 1.) 15 min. -10 deg C. 2.) 2 h, room temp. 3: 89 percent / 63percent HBr / H2O / 8 h / 80 - 90 °C View Scheme