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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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Updated: Jun 5, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

2,6-Dichloro-phenyl 4-methyl-benzoate.

B Thimme Gowda, Sabine Foro, K S Babitha

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

The crystal structure of 2,6-dichlorophenyl 4-methylbenzoate (26DCP4MeBA) was analyzed. Its molecular structure and packing are similar to related aryl benzoates, with a notable dihedral angle between its rings.

Area of Science:

Crystallography
Organic Chemistry

Background:

Aryl benzoates are a class of organic compounds with diverse applications.
Understanding the structure-property relationships of these compounds is crucial for materials science.
Previous studies have characterized various substituted phenyl benzoates.

Purpose of the Study:

To determine and analyze the crystal structure of 2,6-dichlorophenyl 4-methylbenzoate (26DCP4MeBA).
To compare the structural parameters of 26DCP4MeBA with related aryl benzoates.
To investigate the molecular packing in the solid state.

Main Methods:

Single-crystal X-ray diffraction was employed to elucidate the molecular structure.
Bond parameters and dihedral angles were analyzed.
Crystal structure analysis was performed to understand intermolecular interactions and packing.

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Main Results:

The crystal structure of 26DCP4MeBA (C(14)H(10)Cl(2)O(2)) was successfully determined.
The dihedral angle between the benzene and benzoyl rings in 26DCP4MeBA is 77.97(9)°, which differs from related compounds like PBA, 26DCPBA, and 24DCP4MeBA.
Molecules are arranged in zigzag chains within the bc plane.

Conclusions:

The structural analysis of 26DCP4MeBA provides insights into the conformational preferences of substituted aryl benzoates.
The observed dihedral angle suggests specific electronic and steric effects influencing the molecular geometry.
The zigzag chain packing indicates potential for directional intermolecular interactions.