Waiting
Login-Verarbeitung ...

Trial ends in Request Full Access Tell Your Colleague About Jove

18.30: Benzene to Phenol via Cumene: Hock Process

TABLE OF
CONTENTS
JoVE Core
Organic Chemistry

Ein Abonnement für JoVE ist erforderlich, um diesen Inhalt ansehen zu können. Melden Sie sich an oder starten Sie Ihre kostenlose Testversion.

Education
Benzene to Phenol via Cumene: Hock Process
 
TRANSCRIPT

18.30: Benzene to Phenol via Cumene: Hock Process

The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene hydroperoxide radical reacts with another cumene molecule to yield cumene hydroperoxide, regenerating the benzylic radical. In the subsequent protonation step, cumene hydroperoxide gives an oxonium ion. Further, a hydrolytic rearrangement migrates the phenyl group to oxygen (with the loss of water) to yield the carbocation. Finally, the addition of water and a subsequent rearrangement involving a proton shift gives phenol as the product.

Tags

Phenol Benzene Cumene Cumene Hydroperoxide Friedel-Crafts Alkylation Radical Chain Reaction Benzylic Radical Oxonium Ion Hydrolytic Rearrangement Hock Process

Get cutting-edge science videos from JoVE sent straight to your inbox every month.

Waiting X
Simple Hit Counter