ammonium chloride; zinc in ethanol; water 12 h; Ambient temperature;

1: 50 percent / sodium nitrite, phloroglucinol dihydrate, urea / dimethylformamide / 96 h / Ambient temperature 2: 35 percent / Triton B / tetrahydrofuran / 5 h / 0 °C 3: 76 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 4: 81 percent / zinc dust, ammonium chloride / ethanol; H2O / 12 h / Ambient temperature View Scheme

1: 35 percent / Triton B / tetrahydrofuran / 5 h / 0 °C 2: 76 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 3: 81 percent / zinc dust, ammonium chloride / ethanol; H2O / 12 h / Ambient temperature View Scheme

air; ammonium chloride; copper dichloride 1.) Et2O, 35 deg C, 2.) H2O, 3.) CH3OH, 15 deg C; Yield given. Multistep reaction;