1: 1.) 50percent NaH in min. oil / 1.) 1,2-dimethoxyethane, 2 hrs, rt 2.) 1,2-dimethoxyethane, 24 hrs, rt 2: 33 percent / NaCl, H2O / dimethylsulfoxide / 7.5 h / 180 °C / In a sealed tube 3: 65 percent / H2 / 5percent Pd-CaCO3 / ethanol View Scheme

1: 1.) 50percent NaH in min. oil / 1.) 1,2-dimethoxyethane, 1 hr, rt 2.) 1,2-dimethoxyethane, 24 hrs, reflux 2: 80 percent / 47percent HBr / acetic acid; H2O / 15 h / Heating View Scheme