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Process for producing 4-hydroxydiphenyl ether

A technology of hydroxydiphenyl ether and acyl diphenyl ether, which is applied in the field of preparation of 4-hydroxydiphenyl ether, can solve the problems of low reactivity, high temperature and long process procedures, etc., and achieve the effect of high-efficiency preparation

Inactive Publication Date: 2006-11-15
SUMITOMO CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods have problems such as low reactivity and high temperature required, and long process steps, so it is difficult to say that they are the best methods for industrial production.

Method used

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  • Process for producing 4-hydroxydiphenyl ether
  • Process for producing 4-hydroxydiphenyl ether
  • Process for producing 4-hydroxydiphenyl ether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] 1) Put 0.17g (1.0mmol) of diphenyl ether, 0.5mL of o-dichlorobenzene and 0.16g (1.2mmol) of aluminum chloride into a nitrogen-substituted 50mL eggplant flask, and add 0.09g of it while stirring at 50°C (1.1 mmol) Acetyl chloride. After stirring at the same temperature for 3 hours to react, it was cooled to room temperature, 10 mL of water was added, and extracted with 20 mL of diethyl ether. After drying the organic layer with sodium sulfate, the sodium sulfate was filtered off, and the obtained organic layer was concentrated to obtain an oily substance containing 4-acetyldiphenyl ether. This oil was purified by thin-layer chromatography (developing solution: hexane / ethyl acetate) to obtain 0.21 g of 4-acetyldiphenyl ether. Yield: 98%.

[0052] 2) Put 0.17g (1.0mmol) of diphenyl ether, 2mL of 1,2-dichloroethane and 0.27g (2mmol) of aluminum chloride into a nitrogen-substituted 50mL eggplant flask, and stir at 80°C 0.12 g (1.2 mmol) of acetic anhydride was added. Aft...

Embodiment 2

[0058] Add 4mL of acetic acid and 0.1mL of sulfuric acid into 0.21g (1.0mmol) of 4-acetyl diphenyl ether obtained in 3) of Example 1, then add 0.25g (2.2mmol) of 30% aqueous hydrogen peroxide, and stir at 50°C 8 hours. Quantification of the reaction solution by LC revealed that the yield of 4-hydroxydiphenyl ether was 73%, that is, 4-acetoxydiphenyl ether was contained corresponding to a yield of 11%.

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Abstract

A process for producing 4-hydroxydiphenyl ether, characterized by reacting diphenyl ether with an acylating agent in the presence of an acid catalyst to yield a 4-acyldiphenyl ether represented by the formula (1): (wherein R represents (un)substituted alkyl or aryl), reacting the 4-acyldiphenyl ether with a peroxide to yield a 4-acyloxydiphenyl ether represented by the formula (2): (wherein R has the same meaning as defined above), and solvolyzing the ester bond of the 4-acyloxydiphenyl ether.

Description

technical field [0001] The present invention relates to the preparation method of 4-hydroxy diphenyl ether. Background technique [0002] 4-Hydroxydiphenyl ether is a compound useful as an intermediate for pesticides, medicines, fragrances, plastics, and the like. The example of the preparation method of described 4-hydroxydiphenyl ether has: the condensation reaction of phenol and 4-hydroxyl halobenzene (such as Japanese Patent Laid-Open No. 47-34324); the condensation reaction of phenol or halobenzene and hydroquinone (such as Japanese Patent Application No. 55-62033, Japanese Patent Application No. 56-135437); condensation reaction of 4-isopropylphenol and halogenated benzene and subsequent cumene method (such as Japanese Patent Application No. 56-59726); A method of forming a new ether bond between phenyl groups such as condensation reaction of phenol and 4-nitrohalobenzene, reduction of nitro group, and decomposition of diazo (for example, JP-A-53-56630 ) is carried ou...

Claims

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Application Information

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IPC IPC(8): C07C41/26C07C43/23C07C43/263C07C43/295C07C45/46C07C49/84
CPCC07C41/26C07C45/46C07C49/84C07C43/295C07C43/235
Inventor 河本一郎西田寿美雄
Owner SUMITOMO CHEM CO LTD
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