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Hydrolysis of Chlorobenzene to Phenol: Dow Process

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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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Related Experiment Video

Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

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Published on: January 19, 2016

Propyl 4-hydroxy-benzoate.

Yiwen Zhou¹, Guzalnur Matsadiq, Yanling Wu

¹Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This summary is machine-generated.

This study describes the crystal structure of a C(10)H(12)O(3) compound, revealing molecular chains formed by hydrogen bonds and linked by pi-pi interactions between benzene rings.

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Area of Science:

Crystallography
Molecular structure analysis
Organic chemistry

Background:

Understanding the intermolecular forces governing crystal packing is crucial for predicting material properties.
The title compound, C(10)H(12)O(3), was investigated to elucidate its solid-state arrangement.

Purpose of the Study:

To determine the crystal structure of the title compound, C(10)H(12)O(3).
To analyze the intermolecular interactions responsible for the observed crystal packing.

Main Methods:

Single-crystal X-ray diffraction was employed to collect diffraction data.
The crystal structure was solved and refined using standard crystallographic software.

Main Results:

The asymmetric unit contains two molecules of C(10)H(12)O(3).
Molecules form chains along the [010] direction via O-H⋯O hydrogen bonds.
Adjacent chains are interconnected by weak π-π interactions between benzene rings, with a centroid-centroid distance of 4.040(2) Å.

Conclusions:

The crystal structure is stabilized by a combination of hydrogen bonding and π-π stacking interactions.
These interactions dictate the overall supramolecular architecture of the title compound in the solid state.