hydrogenchloride; ethanol in water T=20°C;

hydrogen; platinum(IV) oxide; palladium on activated charcoal in ethanol 24 h; Ambient temperature;

1: 94 percent / conc. H2SO4 / 7 h / Heating 2: 94 percent / K2CO3 / dimethylformamide / 24 h / 80 °C 3: DIBALH / CH2Cl2 / 0.5 h / -78 °C 4: 4 Angstroem molecular sieves / CH2Cl2 / 2.5 h / Ambient temperature 5: hydrogen / 1.) PtO2; 2.) Pd/C / 1.) aq. EtOH; 2.) aq. EtOH, 6 h View Scheme

1: 94 percent / K2CO3 / dimethylformamide / 24 h / 80 °C 2: DIBALH / CH2Cl2 / 0.5 h / -78 °C 3: 4 Angstroem molecular sieves / CH2Cl2 / 2.5 h / Ambient temperature 4: hydrogen / 1.) PtO2; 2.) Pd/C / 1.) aq. EtOH; 2.) aq. EtOH, 6 h View Scheme

1: 4 Angstroem molecular sieves / CH2Cl2 / 2.5 h / Ambient temperature 2: hydrogen / 1.) PtO2; 2.) Pd/C / 1.) aq. EtOH; 2.) aq. EtOH, 6 h View Scheme

1: DIBALH / CH2Cl2 / 0.5 h / -78 °C 2: 4 Angstroem molecular sieves / CH2Cl2 / 2.5 h / Ambient temperature 3: hydrogen / 1.) PtO2; 2.) Pd/C / 1.) aq. EtOH; 2.) aq. EtOH, 6 h View Scheme

hydrogen; platinum(IV) oxide; palladium on activated charcoal 1.) aq. EtOH; 2.) aq. EtOH, 6 h; Yield given. Multistep reaction;