hydrogenchloride; hydrogen; palladium on activated charcoal in ethanol; water T=40°C;

1: sodium ethoxide / ethanol / 3 h / Heating 2: 2.) hydrochloric acid / 1.) water, ethanol, reflux, 60 h; 2.) water, reflux, 30 h 3: 1.) sodium ethoxide / 1.) ethanol, 20 min; 2.) ethanol, dimethylformamide, 90 deg C, 3 h 4: 75 percent / hydrogen, 2N hydrocloric acid / 10percent Pd/C / ethanol; H2O / 40 °C View Scheme

1: 1.) sodium ethoxide / 1.) ethanol, 20 min; 2.) ethanol, dimethylformamide, 90 deg C, 3 h 2: 75 percent / hydrogen, 2N hydrocloric acid / 10percent Pd/C / ethanol; H2O / 40 °C View Scheme

1: sodium ethoxide / ethanol / 3 h / Heating 2: 2.) hydrochloric acid / 1.) water, ethanol, reflux, 60 h; 2.) water, reflux, 30 h 3: 1.) sodium ethoxide / 1.) ethanol, 20 min; 2.) ethanol, dimethylformamide, 90 deg C, 3 h 4: 75 percent / hydrogen, 2N hydrocloric acid / 10percent Pd/C / ethanol; H2O / 40 °C View Scheme

1: 2.) hydrochloric acid / 1.) water, ethanol, reflux, 60 h; 2.) water, reflux, 30 h 2: 1.) sodium ethoxide / 1.) ethanol, 20 min; 2.) ethanol, dimethylformamide, 90 deg C, 3 h 3: 75 percent / hydrogen, 2N hydrocloric acid / 10percent Pd/C / ethanol; H2O / 40 °C View Scheme

1: chromium trioxide / acetic acid; H2O / 30 h / Heating 2: 75 percent / hydrogen, 2N hydrocloric acid / 10percent Pd/C / ethanol; H2O / 40 °C View Scheme