Preparation of Phenol From Cumene (Isopropylbenzene)

$$\text{Cumene} \xrightarrow{\text{O}_2} \text{Cumene Hydroperoxide} \xrightarrow{\text{H}_3\text{O}^+} \text{Phenol} + \text{Acetone (By-product)}$$

Concept

This is the primary industrial method for manufacturing phenol globally (Cumene Process). Isopropylbenzene (cumene) undergoes free-radical auto-oxidation with atmospheric oxygen to form cumene hydroperoxide, which then undergoes acid-catalyzed rearrangement (via a 1,2-phenyl shift to an electron-deficient oxygen atom) to yield phenol and acetone.