Preparation method of 4-(4-hydroxyphenyl) cyclohexanone

A technology of hydroxyphenyl and cyclohexanone, which is applied in the field of preparation of 4-cyclohexanone, can solve the problems of large environmental pollution, high preparation cost, and low yield, and achieve high safety, low production cost, and high yield. high effect

Inactive Publication Date: 2019-07-19
宁夏中星显示材料有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Aiming at the problems of low yield, high environmental pollution and high production cost in the process for preparing 4-(4-hydroxyphenyl)cyclohexanone in the prior art, the invention provides a 4-(4-hydroxyphenyl)cyclohexanone Method for the preparation of ketones

Method used

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  • Preparation method of 4-(4-hydroxyphenyl) cyclohexanone
  • Preparation method of 4-(4-hydroxyphenyl) cyclohexanone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] A kind of preparation method of 4-(4-hydroxyphenyl) cyclohexanone:

[0061] Step 1. Put 346g of p-bromophenol and 242.9g of triethylamine in a 3000ml three-necked flask, add 1000mL of dichloromethane, stir well, and add the dichloromethane solution of trimethylchlorosilane dropwise in an ice-salt bath at 0°C (250g of trimethylchlorosilane dissolved in 700mL of dichloromethane), the temperature control does not exceed 30°C, after 60 minutes of dropwise addition, a white salt appears in the system, the temperature of the water bath is raised to 30°C, stirred for 3h, and 600ml of water is added to the system, After stirring for 30 minutes, after-treatment, 463.48 g of p-trimethylsilyloxybromobenzene was obtained as a colorless and transparent liquid, with a yield of 94.6% and a purity of 99.3%;

[0062] Step 2. Under the protection of nitrogen, put 8.7g of magnesium chips in a 500mL three-necked flask, and put it in a water bath at 40°C. Dissolve 73.5g of the p-trimethylsi...

Embodiment 2

[0069] A kind of preparation method of 4-(4-hydroxyphenyl) cyclohexanone:

[0070] Step 1. Put 346g of p-bromophenol and 237.3g of pyridine in a 3000ml three-neck flask, add 1038mL of toluene, stir well, and add the toluene solution of methylal dropwise under the condition of ice-salt bath (182.6g of methylal is dissolved in 913mL of toluene middle), temperature control does not exceed 50°C, after 60 minutes of dropwise addition, white salt appears in the system, stir and react at 30°C for 1 hour, add 600ml of water to the system, stir for 30 minutes, post-treatment can get the compound shown in formula I 417.07g of methoxymethoxybromobenzene is a colorless transparent liquid with a yield of 96.1% and a purity of 99.5%;

[0071]

[0072] Step 2. Under the protection of nitrogen, place 7.56g of magnesium chips in a 500mL three-necked flask, and put it in an ice-salt bath at 0°C. Dissolve 65.1g of p-methoxymethoxybromobenzene prepared above in 148mL of ether, and add dropwise...

Embodiment 3

[0079] A kind of preparation method of 4-(4-hydroxyphenyl) cyclohexanone:

[0080] Step 1. Put 346g of p-bromophenol and 424g of sodium carbonate in a 3000ml there-necked flask, add 1730mL of dichloroethane, stir well, and add dropwise the dichloroethane solution of dihydropyran (252.4g Dissolve dihydropyranane in 758mL dichloroethane), control the temperature not to exceed 40°C, after 50min dropwise addition, a white salt appears in the system, stir and react at 30°C for 4h, add 600ml water to the system, stir for 30min , post-processing can obtain 474.72 g of a colorless and transparent liquid of p-bromophenol tetrahydropyranyl ether shown in formula II, with a yield of 91.6% and a purity of 99.4%;

[0081]

[0082] Step 2. Under the protection of nitrogen, put 8.1g of magnesium chips in a 500mL three-necked flask, in a water bath at 30°C, and dissolve 77.4g of p-bromophenol tetrahydropyranyl ether prepared above in 253mL of methyl tert-butyl ether, Add dropwise to the t...

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Abstract

The invention relates to the technical field of chemical synthesis, in particular to a preparation method of 4-(4-hydroxyphenyl) cyclohexanone. According to the preparation method, p-bromophenol is used as a raw material, a Grignard reagent is prepared through hydroxyl protection and Grignard reaction, then the prepared Grignard reagent is utilized to couple with 1,4-cyclohexanedione monoethyleneglycol ketal, then the product is dehydrated to obtain alkene, and double protecting groups are removed after hydrogenation to prepare a target product, namely, 4-(4-hydroxyphenyl) cyclohexanone. Thepreparation method of 4-(4-hydroxyphenyl) cyclohexanone, provided by the invention, has the advantages of reasonable process design, high yield and low production cost; the prepared 4-(4-hydroxyphenyl) cyclohexanone is a white solid, the HPLC content is more than 99.5%, the total yield of the product can reach 75-80%, and the raw materials are easy to obtain; and the method has simple operation and high safety, and realizes industrial production of 4-(4-hydroxyphenyl) cyclohexanone.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method of 4-(4-hydroxyphenyl)cyclohexanone. Background technique [0002] 4-(4-hydroxyphenyl)cyclohexanone, the structural formula is: [0003] [0004] Molecular formula is C 12 h 14 o 2 , is a white solid, an important chemical and pharmaceutical intermediate, and an important intermediate for the preparation of various liquid crystal materials. In recent years, with the rapid development of the liquid crystal industry and the pharmaceutical industry, the demand for 4-(4-hydroxyphenyl)cyclohexanone is increasing year by year. [0005] In existing literature reports, the synthetic route of synthesizing 4-(4-hydroxyphenyl)cyclohexanone is mainly based on 4,4'-diphenol as raw material, which is reduced to 4-(4-hydroxycyclohexanone by reducing agent. Alk)phenol, protected by benzyl chloride to obtain 4-(4-benzyloxyphenyl)cyclohexanol, oxidized to ob...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/59C07C49/747
CPCC07C45/59C07D317/06C07F3/02C07C41/56C07D309/12C07F7/1804C07F7/188C07C2601/14Y02P20/55
Inventor 岳刚王志强丁秋月禹凯王利民陈少华关登仕
Owner 宁夏中星显示材料有限公司
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