1: 98 percent / diethyl ether 2: HCl / diethyl ether / 15 h / Ambient temperature 3: 10percent Pd/C / 12 h / 280 - 290 °C View Scheme

1: 98 percent / diethyl ether 2: HCl / diethyl ether / 15 h / Ambient temperature 3: 58 percent / 10percent Pd/C / 12 h / 280 - 290 °C 4: 30 percent / LAH/AlCl3 View Scheme

1: 98 percent / diethyl ether 2: HCl / diethyl ether / 15 h / Ambient temperature 3: diethyl ether / 1.) ether, room temp., 6 h, 2.) reflux, 1 h 4: 1.) anhydrous CuSO4, 2.) H2 / 2.) 5percent Pd/C / 1.) 120 deg C, 1 h, 2.) acetic acid, 50 deg C, 40 psi View Scheme

1: 98 percent / diethyl ether 2: HCl / diethyl ether / 15 h / Ambient temperature 3: 58 percent / 10percent Pd/C / 12 h / 280 - 290 °C 4: LAH/AlCl3 View Scheme