Convert phenol to benzyl chloride

How to convert phenol to benzyl chloride?

Conversion of phenol to benzyl chloride may occur in two ways. The first one is direct method which consists of five or six steps and the second method occur via benzene nucleus.

In the first method, phenol reacts with ammonia at 300ᵒC in presence of anhydrous ZnCl₂ to form aniline which under goes diazotization reaction at very low temperature, resulting in the formation of benzene diazonium chloride salt.

The producing benzene diazonium chloride salt under goes sand mayer reaction followed by reduction by lithium aluminium hydride gives benzyl amine.

Reaction of benzyl amine with nitrous acid gives benzyl alcohol which reacts with PCl₃ or SOCl₂ produce the expected product, benzyl chloride.

In the second method, on heating of phenol with zinc dust benzene is obtained. Now benzene under goes Friedel craft reaction in presence of anhydrous AlCl₃ and methyl chloride forms toluene.

When a mixture of toluene and chlorine is heated at 110ᵒC, the expected product, benzyl chloride is obtained.

Summary:

How to convert phenol to benzyl chloride?

How to convert phenol to benzyl chloride via benzene?

How to convert phenol to benzyl chloride without involving benzene?

Why is phenol acidic in nature ?