1: 72 percent / H2 / 5percent Pd/C / acetic acid / 24 h / 60 °C / 2844.3 - 3102.9 Torr 2: 98 percent / diethyl ether 3: HCl / diethyl ether / 15 h / Ambient temperature 4: diethyl ether / 1.) ether, room temp., 6 h, 2.) reflux, 1 h 5: 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: 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: HCl / diethyl ether / 15 h / Ambient temperature 2: diethyl ether / 1.) ether, room temp., 6 h, 2.) reflux, 1 h 3: 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: diethyl ether / 1.) ether, room temp., 6 h, 2.) reflux, 1 h 2: 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

hydrogen; palladium on activated charcoal in ethyl acetate Title compound not separated from byproducts;

hydrogen; copper(II) sulfate; palladium on activated charcoal 1.) 120 deg C, 1 h, 2.) acetic acid, 50 deg C, 40 psi; Yield given. Multistep reaction;