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A kind of preparation method of 2,2'-dihydroxybenzophenone compounds

A technology for dihydroxybenzophenone and compounds, which is applied in the field of synthesis of ketone acyclic compounds, can solve the problems of high raw material requirements and expensive Grignard reagents, and achieve the effects of high purity, easy availability of raw materials, and high yield

Active Publication Date: 2020-12-11
北京吉海川科技发展有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0029] This method is simple to operate, only one-step reaction, but requires high raw materials, Grignard reagents are more expensive

Method used

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  • A kind of preparation method of 2,2'-dihydroxybenzophenone compounds
  • A kind of preparation method of 2,2'-dihydroxybenzophenone compounds
  • A kind of preparation method of 2,2'-dihydroxybenzophenone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Example 1: Preparation of 5-methyl-3-[5-methyl-2-hydroxyphenyl]benzofuran-2-(3hydro)-one (p-methyllactone)

[0056] 21.6g of p-cresol (0.2 mole), 9.2g of glyoxylic acid monohydrate (0.1 mole) and 0.3 g of p-toluenesulfonic acid were placed in a 500ml there-necked flask, 200ml of toluene was added, and a magnetic stirring belt was added after the heating was fully dissolved. The water was refluxed for 6 hours, and the liquid phase followed the reaction. After the reaction was completed, the solvent was evaporated to dryness to obtain a yellow-brown solid, which was then recrystallized with methanol to obtain 22.5 g of a light-yellow solid, that is, 5-methyl-3-[5-methyl- 2-Hydroxyphenyl]benzofuran-2-(3hydro)-one, referred to as methyl lactone, has a liquid phase purity of 98.3% and a yield of 90.1%.

[0057] Product structure verification (see Figures 1A-1E ):

[0058] 1 HNMR(δ,ppm,400MHz,CDCl 3 ): 2.239(s,3H,CH 3 ); 2.321(s,3H,CH 3 ); 4.983(s, 1H); 5.059(s, 1H); 6...

Embodiment 2

[0063] Example 2: Preparation of 5-ethyl-3-[5-ethyl-2-hydroxyphenyl]benzofuran-2-(3hydro)-one (p-ethyllactone)

[0064] Place 24.4g p-ethylphenol (0.2 mol), 9.2g glyoxylic acid monohydrate (0.1 mol) and 0.3 gram p-toluenesulfonic acid in a 500ml there-necked flask, add 200ml toluene, and heat it with a magnetic stirring belt after it is completely dissolved. The water was refluxed for 6 hours, and the liquid phase followed the reaction. After the reaction was complete, the solvent was evaporated to dryness to obtain a yellow-brown solid, which was then recrystallized with ethanol to obtain 25.6 g of a light-yellow solid, namely 5-ethyl-3-[5-ethyl-2 -Hydroxyphenyl]benzofuran-2-(3hydro)-one, referred to as ethyl lactone, the liquid phase purity of the ethyl lactone is 98.5%, and the yield is 92.0%.

[0065] Product structure verification (see Figures 2A-2E ):

[0066] 1 HNMR(δ,ppm,400MHz,CDCl 3 ): 1.182(m, 6H, CH 3 ); 2.536(q, 2H); 2.613(q, 2H); 4.679(s, 1H); 5.081(s, 1H)....

Embodiment 3

[0071] Example 3: Preparation of 5-isopropyl-3-[5-isopropyl-2-hydroxyphenyl]benzofuran-2-(3hydro)-one (p-isopropyllactone)

[0072] Place 27.2g of p-isopropylphenol (0.2 mole), 9.2g of glyoxylic acid monohydrate (0.1 mole) and 0.3 g of p-toluenesulfonic acid in a 500ml three-necked flask, add 200ml of toluene, and stir magnetically after heating and dissolving. The reaction was carried out under reflux with water for 6 hours, and the liquid phase followed the reaction. After the reaction was completed, the solvent was evaporated to dryness to obtain a yellow-brown solid, which was then recrystallized with ethanol to obtain 27.3 g of a light-yellow solid, namely 5-isopropyl-3-[5-isopropyl] Base-2-hydroxyphenyl]benzofuran-2-(3-hydro)-one, referred to as propyl lactone, the liquid phase purity of the propyl lactone is 98.7%, and the yield is 89.2%.

[0073] Product structure verification (see Figures 3A-3E ):

[0074] 1 HNMR(δ,ppm,400MHz,CDCl 3 ): 1.170 (m, 6H); 1.227 (d, 6H...

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Abstract

The invention relates to a preparation method of a 2,2'-dihydroxy diphenyl ketone compound. The method belongs to the technical field of ketone acyclic compound synthesis, and comprises the steps of adopting 5-alkyl-3-[5-alkyl-2-hydroxycyclohexyl phenyl ketone]benzofuran-2-(3 hydrogen)-ketone as a raw material, dissolving in a solvent, adding an anhydrous alkali catalyst, feeding oxygen or air, and carrying out oxidation reaction. The preparation method provided by the invention is applied to preparing the dihydroxy diphenyl ketone compound and has the advantages of concise steps, green synthesis without pollution, high yield and the like.

Description

technical field [0001] The application relates to a preparation method of 2,2'-dihydroxybenzophenone compounds, belonging to the technical field of ketone acyclic compound synthesis. Background technique [0002] Benzophenone compounds have been widely used in pharmaceuticals, pesticides, plastics, dyes, electronic chemicals and daily chemicals. With the different types, numbers and positions of substituents on the benzene ring on both sides of the carbonyl group, the benzophenone family members are very large, and compounds with hydroxyl groups on the benzene ring are also commonly used as antioxidants. Therefore, it is of great significance to study the synthesis of such compounds. [0003] At present, the main synthesis methods are: Fielder-Crafts reaction, transition metal catalysis, oxidation method, photocatalysis method, etc. The details are as follows: [0004] 1. Using benzene and benzoyl chloride as raw materials, anhydrous aluminum trichloride as catalyst, heati...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/83C07C45/32
CPCC07C45/32C07C49/83
Inventor 焦凤鸣沈润溥王彦荣李英杰张符刘健盛国栋常凯凯徐慧婷肖慧泉
Owner 北京吉海川科技发展有限公司
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