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Preparation method of diaryl ketone

A technology of diaryl ketones and aryl groups is applied in the field of preparation of diaryl ketones and achieves the effects of high yield, readily available raw materials and simple and convenient operation.

Active Publication Date: 2022-02-18
SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In contrast, using cheap and easy-to-obtain compounds to prepare diaryl ketone compounds through efficient and practical synthetic methods undoubtedly has obvious advantages, but there are no related reports in the prior art

Method used

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  • Preparation method of diaryl ketone
  • Preparation method of diaryl ketone
  • Preparation method of diaryl ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: aryl is p-tert-butylphenyl, the method for preparing diaryl ketone, the steps are as follows:

[0032] (1) Preparation of 1,1,4,4-tetra-tert-butylphenylbutadiol

[0033] Yield: 65.6%, m.p.: 243-245°C; 1 H NMR (400MHz, Chloroform-d) δ7.37(d, J=8.5Hz, 4H), 7.25(d, J=8.1Hz, 12H), 4.67(s, 2H), 4.47(d, J=4.7Hz ,2H),3.72(d,J=4.5Hz,2H),1.36(s,18H),1.22(s,18H). 13 C NMR (101MHz, Chloroform-d) δ149.9, 149.7, 141.2, 141.1, 141.0, 125.4, 125.2, 124.6, 81.4, 72.4, 34.5, 34.3, 31.4, 31.2.

[0034] (2) Preparation of p-tert-butylphenyl dichlorocyclosulfite

[0035] In a round-bottomed flask, 1,1,4,4-tetra-tert-butylphenylbutanetetraol solution in tetrahydrofuran and 30 equivalents (that is, 1,1,4,4-tetra-tert-butylphenylbutanetetraol The molar ratio of triethylamine to triethylamine is 1:30, the same below), and after stirring at 0°C for 15 minutes, 3 equivalents of thionyl chloride (that is, 1,1,4,4-tetra-tert-tert The molar ratio of butylphenyl butanetetraol to...

Embodiment 2

[0039] Embodiment 2: aryl is p-methylphenyl, the method for preparing diaryl ketone, the steps are as follows:

[0040] (1) Preparation of 1,1,4,4-tetra-p-methylphenylbutanetetraol

[0041] (400MHz,Chloroform-d)δ7.20(s,4H,Ar-H),7.15(s,8H,Ar-H),7.06(s,4H,Ar-H)4.68(s,2H,OH), 4.41(s,2H,CH),3.80(s,2H,OH),2.36(s,6H,CH3),2.24(s,6H,CH3). 13 C NMR (101MHz, DMSO-d 6 )δ143.9, 143.1, 135.8, 135.4, 129.0, 128.5, 126.7, 125.8, 81.4, 71.8.

[0042] (2) Preparation of p-methylphenyl dichlorocyclosulfite

[0043] In a round-bottomed flask, 1,1,4,4- tetrahydrofuran solution of tetra-p-methylphenyl butanetetraol and 30 equivalents of triethylamine were stirred at 0°C for 15 minutes, and then 3 equivalents of chlorinated ethylene chloride were added dropwise. Sulfone, after stirring for 30 minutes, return to room temperature (25-30°C), continue stirring for 30 minutes, add water (remove the triethylamine salt), and recrystallize with ethanol to obtain p-methylphenyl dichlorocyclosulfurous ...

Embodiment 3

[0046] Embodiment 3: aryl is p-trifluoromethylphenyl, the method for preparing diaryl ketone, the steps are as follows:

[0047] (1) Preparation of 1,1,4,4-tetrafluoromethylphenylbutanetetraol

[0048] 32%, m.p.:135-136℃, 1 H NMR(400MHz,Chloroform-d):δ7.66-7.42(m,16H,Ar-H),4.63(s,2H,OH),4.46(s,2H,CH),3.84(s,2H,OH ). 13 C NMR (101MHz, DMSO-d 6 )δ151.0, 149.2, 128.2, 127.0, 125.3, 124.9, 80.8, 70.9.

[0049] (2) Preparation of p-trifluoromethylphenyl dichlorocyclosulfite

[0050] In a round-bottomed flask, 1,1,4,4-tetrafluoromethylphenylbutanol tetrahydrofuran solution and 30 equivalents of triethylamine were stirred at 0°C for 15 minutes, and then 3 equivalents of chlorine were added dropwise. sulfoxide, stirred for 30 minutes and then returned to room temperature (25-30°C), continued to stir for 30 minutes, then added water (to remove the generated triethylamine salt), and recrystallized with ethanol to obtain p-trifluoromethylphenyl dichloride Cyclic sulfites. Ar=4-...

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Abstract

The invention relates to the field of organic compound preparation chemistry, and particularly discloses a preparation method of diaryl ketone. The preparation method comprises the following steps: reacting tartrate with an aryl Grignard reagent to prepare 1,1,4,4-tetraaryl butantetraol; the method comprises the following steps: in the presence of an organic alkali and under a specific temperature condition, carrying out a highly regioselective 2, 3-cyclic sulfite esterification reaction on the 1,1,4,4-tetraaryl butantetraol and thionyl chloride to generate dichloro aryl cyclic sulfite; and reacting the dichloro aryl cyclic sulfite with inorganic alkali liquor at a certain temperature in a certain organic solvent to generate the diaryl ketone. The preparation method avoids the use of an expensive heavy metal-containing catalyst, and has the remarkable characteristics of easily available raw materials, simplicity and convenience in operation, excellent reaction region selectivity, easiness in treatment, high yield and the like.

Description

technical field [0001] The invention relates to the field of organic compound preparation chemistry, in particular to a preparation method of diaryl ketone. Background technique [0002] As a class of very important chemical products and pharmaceutical intermediates, diaryl ketones are widely used in the synthesis of fine chemicals such as drugs, pesticides and dyes ((a) Chemical & Pharmaceutical Bulletin, 2004, 52:818; (b) J.M ed.Chem., 1997, 40:3937; (c) invention patent: synthesis process of diaryl ketone derivatives, publication number: 107032938A). The traditional synthesis methods include hydrolysis of cellular dihalides, Friedel-Crafts acylation, oxidation or dehydrogenation of alcohols, preparation of aroyl chlorides with Grignard reagents or organocopper-lithium. The most commonly used method is Friedel-Crafts acylation. In the preparation process, a large amount of Lewis acid catalysts are often required, which increases the processing capacity of metal residues. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/56C07C49/784
CPCC07C45/56C07D327/10C07C49/784
Inventor 胡晓允郭建鑫
Owner SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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