hydrogenchloride; hydrogen; palladium on activated charcoal in methanol

1: 33 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / CH2Cl2 / 0.5 h / 45 °C 2: 84 percent / LiAlH4 / 1,2-dimethoxy-ethane / 1 h 3: 93 percent / conc. HCl / methanol / 0.08 h / 70 °C 4: 73 percent / Pb3O4 / 1 h / Ambient temperature 5: 35 percent / LiAlH4, AlCl3 / 1,2-dimethoxy-ethane / 0.67 h / Ambient temperature View Scheme