mercury dichloride; sodium nitrite

1: p-toluenesulfonic acid / benzene / 6 h / Heating 2: hexane; benzene / 0.5 h / Ambient temperature 3: 3.0 N HCl, NaCl / diethyl ether / 3 h / Ambient temperature 4: H2 / 10percent Pd/C / ethyl acetate / 760 Torr 5: 90 percent / 0.5 N NaOH / ethanol / 6 h / Heating View Scheme

1: p-toluenesulfonic acid / benzene / 6 h / Heating 2: hexane; benzene / 0.5 h / Ambient temperature 3: 3.0 N HCl, NaCl / diethyl ether / 3 h / Ambient temperature 4: H2 / 10percent Pd/C / ethyl acetate / 760 Torr View Scheme

1: p-toluenesulfonic acid / benzene / 6 h / Heating 2: hexane; benzene / 0.5 h / 60 °C 3: 3.0 N HCl, NaCl / diethyl ether / 3 h / Ambient temperature 4: 94 percent / 0.5 N NaOH / ethanol / 6 h / Heating View Scheme

1: p-toluenesulfonic acid / benzene / 6 h / Heating 2: hexane; benzene / 0.5 h / Ambient temperature 3: 3.0 N HCl, NaCl / diethyl ether / 3 h / Ambient temperature View Scheme