Chapter 24: Phenols

Base Hydrolysis of Chlorobenzene

Summary

• This is a useful industrial method for the synthesis of phenol.
• Reagents : Usually NaOH, 350 ^oC followed by an acidic work-up to neutralise the phenoxide.
• The reaction occurs via the elimination-addition mechanism via a benzyne intermediate.
• Elimination of HCl creates the benzyne that then undergoes addition of H₂O to produce the phenol.

• Can you recall how you make chlorobenzene ?