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18.29: Hydrolysis of Chlorobenzene to Phenol: Dow Process

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JoVE Core
Organic Chemistry

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Hydrolysis of Chlorobenzene to Phenol: Dow Process
 
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18.29: Hydrolysis of Chlorobenzene to Phenol: Dow Process

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 intermediate. The benzyne intermediate then reacts with the base, followed by an acid workup that generates phenol as the final product.

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Keywords: Hydrolysis Chlorobenzene Phenol Dow Process Aryl Halides Nucleophiles High Temperature High Pressure Elimination-addition Benzyne Intermediate Sodium Hydroxide Acid Workup

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