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A meta-substituted phenol compound and its preparation method and application

A technology for compounds and phenol derivatives, applied in the field of meta-substituted phenol compounds and their preparation, can solve the problems of low reaction stability, complex reactions, and high synthesis reaction costs, and achieve good atom economy, good selectivity, and ease of use. The effect of further conversion

Active Publication Date: 2022-02-15
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The invention provides a meta-substituted phenol derivative molecule and its preparation method and application, which solves the technical problems of high synthesis reaction cost, low reaction stability and complex reaction of the meso-substituted phenol derivative molecule in the prior art

Method used

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  • A meta-substituted phenol compound and its preparation method and application
  • A meta-substituted phenol compound and its preparation method and application
  • A meta-substituted phenol compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Example 1 3-(phenylamino)phenol (3a)

[0052]

[0053] Under an atmosphere of oxygen at atmospheric pressure, cyclohexanone 1 (59.2mg, 0.50mmol), aniline 2a (18.6mg, 0.20mmol), cuprous oxide (21.0mg, 0.15mmol), tert-butyl Hydroperoxide (135.2mg, 1.5mmol), 2,2,6,6-tetramethylpiperidine oxide (9.4mg, 0.06mmol), iodine (135.2mg, 0.3mmol), toluene (toluene, 2.0mL ), reacted for 12 hours at a temperature of 120°C. After the reaction was completed, it was cooled to room temperature, filtered through diatomaceous earth, and concentrated to obtain a crude product. The crude product was separated by chromatography on a prepared silica gel plate, and the selected developer or eluent was petroleum ether to ethyl acetate at a volume ratio of 10:1 to obtain the product 3-(phenylamino)phenol (3a): white Solid, yield 51% (47.2mg).

[0054] 3-(phenylamino)phenol (3a) proton nuclear magnetic resonance spectrum measurement result is: 1 H NMR (400MHz, CDCl 3 )δ7.43-7.39(m,2H),7.22...

Embodiment 2

[0057] Example 2 3-((4-bromophenyl)amino)phenol (3b)

[0058]

[0059] Under an atmosphere of oxygen at atmospheric pressure, cyclohexanone 1 (58.8mg, 0.60mmol), p-bromoaniline 2b (34.4mg, 0.20mmol), cuprous oxide (21.0mg, 0.15mmol), tert-butyl hydroperoxide (162.2mg, 1.8mmol), 2,2,6,6-tetramethylpiperidine oxide (18.8mg, 0.12mmol), iodine (270.4mg, 0.6mmol), toluene (toluene, 2.5mL), reacted at a temperature of 120°C for 12 hours. After the reaction was completed, it was cooled to room temperature, filtered through diatomaceous earth, and concentrated to obtain a crude product. The crude product was separated by chromatography on a prepared silica gel plate, and the selected developer or eluent was a volume ratio of petroleum ether to ethyl acetate of 10:1 to obtain the product 3-((4-bromophenyl)amino)phenol (3b): white solid, yield 51% (80.8 mg).

[0060] 3-((4-bromophenyl)amino)phenol (3b) proton nuclear magnetic resonance spectrum measurement result is: 1 H NMR (400...

Embodiment 3

[0063] Example 3 3-([1,1'-biphenyl]-4-ylamino)phenol (3c)

[0064]

[0065] Under an atmosphere of oxygen at atmospheric pressure, cyclohexanone 1 (29.4mg, 0.30mmol), 4-amino-1,1'biphenyl 2c (18.6mg, 0.20mmol), cuprous oxide ( 21.0mg, 0.15mmol), tert-butyl hydroperoxide (135.2mg, 1.5mmol), 2,2,6,6-tetramethylpiperidine oxide (9.4mg, 0.06mmol), iodine (135.2mg, 0.3 mmol), toluene (2.0 mL), reacted at a temperature of 80° C. for 20 hours. After the reaction was completed, it was cooled to room temperature, filtered through diatomaceous earth, and concentrated to obtain a crude product. The crude product was chromatographically separated on a prepared silica gel plate, and the selected developer or eluent was a volume ratio of petroleum ether to ethyl acetate of 10:1 to obtain the product 3-([1,1'-biphenyl]- 4-ylamino)phenol (3c): white solid, yield 62% (56.1 mg).

[0066] 3-([1,1'-biphenyl]-4-ylamino)phenol (3c) H NMR spectrum measurement results are: 1 H NMR (400MHz, CDC...

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Abstract

The invention relates to the field of organic synthesis, in particular to a meta-substituted phenol derivative molecule and its preparation method and application. The invention discloses a method for preparing meta-substituted phenol molecules, which comprises performing multiple oxidative dehydrogenation coupling reactions on the compound shown in formula I and the compound shown in formula II to obtain the compound shown in formula III. The invention provides a meta-substituted phenol derivative molecule and its preparation method and application, which solves the technical problems of high synthesis reaction cost, low reaction stability and complex reaction of the meso-substituted phenol derivative molecule in the prior art .

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a meta-substituted phenol compound and its preparation method and application. Background technique [0002] Phenol and its derivatives are an important class of organic substances, which play an important role in the modern chemical and biomedical industries, and are the core structures of many bioactive compounds. Phenol and its derivatives can also be used as commonly used laboratory solvents, reagents and disinfectants. Biologically, the aqueous solution of phenol can also separate proteins and DNA on chromosomes in plant cells and use them as DNA stains for biological experiments. Substituted phenol derivatives are common and important chemicals widely used in the preparation of high-value pharmaceuticals, agrochemicals, polymers, bioactive compounds, and other fine and bulk chemicals. Substituted phenol derivatives usually have three positions that can be substituted: the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C213/00C07C37/20C07C41/30C07C39/15C07C43/23C07C215/76C07B37/04
Inventor 王天璋卢宇靖李先纬霍延平
Owner GUANGDONG UNIV OF TECH