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Related Concept Videos

Benzene to Phenol via Cumene: Hock Process01:27

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...
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Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
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Physical Properties of Alcohols and Phenols02:32

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Alcohols are organic compounds in which a hydroxy group is attached to a saturated carbon. Phenols are a class of alcohols containing a hydroxy group attached to an aromatic ring. The physical properties of the alcohols and phenols are influenced by hydrogen bonding due to the oxygen–hydrogen dipole in the hydroxy functional group and dispersion forces between alkyl or aryl regions of alcohol and phenol molecules.
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Preparation of Alcohols via Substitution Reactions

Overview
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Primary alcohols are synthesized from primary alkyl halides, and the...

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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

High chemoselectivity in the phenol synthesis.

Matthias Rudolph1, Melissa Q McCreery, Wolfgang Frey

  • 1Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.

Beilstein Journal of Organic Chemistry
|August 2, 2011
PubMed
Summary

Researchers failed to trap early intermediates in gold-catalyzed phenol synthesis. Competing reaction steps are faster than interception, explaining the reaction

Keywords:
alcoholsalkenesalkynesfuransgoldketones

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Area of Science:

  • Organic Chemistry
  • Organometallic Chemistry

Background:

  • Gold catalysis is a powerful tool in organic synthesis.
  • Phenol synthesis via gold catalysis is efficient and general.
  • Understanding reaction intermediates is crucial for mechanistic studies.

Purpose of the Study:

  • To investigate the nature of early intermediates in gold-catalyzed phenol synthesis.
  • To determine if trapping experiments can isolate key reactive species.

Main Methods:

  • Utilized various trapping agents (vinyl, ketone, alcohol) in inter- and intramolecular settings.
  • Employed gold catalysis for phenol synthesis.

Main Results:

  • Failed to intercept the proposed gold carbenoid species.
  • Interception reactions were slower than competing pathways.
  • Activation barriers for interception are higher than for competing steps.

Conclusions:

  • The high efficiency and functional group tolerance of gold-catalyzed phenol synthesis are attributed to rapid competing reaction steps over slower interception pathways.
  • Early intermediates in this reaction are highly reactive and transient.