Aniline to benzene organic conversion has two steps. First, benzenediazonium chloride should be prepared by aniline. Then benzene can be prepared by benzenediazonium chloride .
There are two methods to prepare benzene from aniline.
Prepare benzenediazonium chloride from aniline using nitrous acid ( NaNO2 / HCl ) . To benzenediazonium chloride is prepared, temperature should be kept under 50C.
Then add H3PO2 or CH3CH2OH to benzenediazonium chloride to prepare benzene.
There are differences in properties of aniline and benzene. That can used to identify aniline and benzene.
Aniline reacts with bromine liquid and give white precipitate, 2,3,4-tribromoaniline. But benzene does not react with liquid bromine.
Aniline is a primary amine which reacts with dilute acids such as HCl, H2SO4 and give salts. This salt is soluble in water.
But benzene does not react with dilute acids.
Aniline to benzene through phenol has only two steps. First, aniline reacts with nitrous acid in room temperature. It gives phenol. Then phenol is distilled with zinc powder to give benzene.
Nitrous acid - HNO2
Aniline to benzene is a famous conversion.