1: 86.9 percent / NaH / dimethylsulfoxide / 0.5 h / 70 °C 2: hydrogen / 10percent Pd-C / methanol / 760 Torr / Ambient temperature 3: 1.) NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, water, 5 deg C, 30 min, 2.) acetone, water, 35 deg C View Scheme

1: 86.9 percent / NaH / dimethylsulfoxide / 0.5 h / 70 °C 2: hydrogen / 10percent Pd-C / methanol / 760 Torr / Ambient temperature 3: 1.) NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, water, 5 deg C, 30 min, 2.) acetone, water, 35 deg C View Scheme

1: hydrogen / 10percent Pd-C / methanol / 760 Torr / Ambient temperature 2: 1.) NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, water, 5 deg C, 30 min, 2.) acetone, water, 35 deg C View Scheme

copper(I) oxide; hydrogenchloride; sodium nitrite 1.) acetone, water, 5 deg C, 30 min, 2.) acetone, water, 35 deg C; Yield given. Multistep reaction;

1: 91.6 percent / dimethylsulfoxide / 2 h / 100 °C 2: 70.3 percent / 6N HCl / ethanol / 50 h / Heating View Scheme

hydrogenchloride 1.) sulfolane, 120 deg C, 10 h; 2.) sulfolane, 100 deg C, 8 h; Yield given. Multistep reaction;