thionyl chloride; aluminium trichloride in nitrobenzene; benzene

aluminium trichloride in nitrobenzene T=60 - 65°C; 6 h;

1: toluene / 48 h / |Reflux 2: N,N-dimethyl-formamide / 24 h / 70 °C 3: ammonium acetate; methanol / 18 h / 20 °C 4: ethanol / 2 h / 20 °C 5: sodium hydroxide / ethanol / 48 h / 20 °C 6: potassium hydroxide; water / ethanol / 20 h / |Reflux 7: sodium nitrite; hydrogenchloride / water / 0.67 h / 0 - 20 °C View Scheme

1: toluene / 48 h / |Reflux 2: ammonium acetate; methanol / 18 h / 20 °C 3: ethanol / 2 h / 20 °C 4: sodium hydroxide / ethanol / 48 h / 20 °C 5: potassium hydroxide; water / ethanol / 20 h / |Reflux 6: sodium nitrite; hydrogenchloride / water / 0.67 h / 0 - 20 °C View Scheme