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Benzene to Phenol via Cumene: Hock Process

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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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Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
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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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Phenyl 3-meth-oxy-4-phen-oxy-benzoate.

Jing Zhou¹, Shuai Zheng, Gang Chen

¹College of Science, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|November 8, 2011

Summary

This summary is machine-generated.

This study details the molecular structure of C(20)H(16)O(4), revealing specific dihedral angles between its phenyl and central benzene rings. The crystal structure analysis shows molecules forming ribbons through weak intermolecular interactions.

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Area of Science:

Crystallography
Organic Chemistry
Molecular Structure Analysis

Background:

Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
The specific molecule C(20)H(16)O(4) has potential applications where precise molecular conformation is key.

Purpose of the Study:

To elucidate the detailed molecular geometry of C(20)H(16)O(4).
To investigate the intermolecular interactions and packing in the solid state.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the precise atomic coordinates.
Analysis of dihedral angles and intermolecular contacts (C-H⋯O) was performed.

Main Results:

The two terminal phenyl rings exhibit significant dihedral angles of 79.80°(7) and 69.35°(7) relative to the central benzene ring.
The crystal structure is characterized by the formation of molecular ribbons facilitated by weak intermolecular C-H⋯O interactions along the [110] direction.

Conclusions:

The determined molecular conformation and crystal packing provide fundamental insights into the solid-state behavior of C(20)H(16)O(4).
These findings contribute to the understanding of structure-property relationships in related organic compounds.