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Synthesis method of 3'-acyl-2,4'-dihydroxyl diphenyl ketone compound

A technology for bishydroxybenzophenone and a synthesis method is applied in the separation/purification of carbonyl compounds, preparation of heterocyclic compounds, organic chemistry, etc., and can solve the problems of harsh reaction conditions, low atom economy, poor regioselectivity, etc., To achieve the effect of simple operation, high atom economy and mild conditions

Active Publication Date: 2017-09-08
HENAN NORMAL UNIV
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  • Description
  • Claims
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Problems solved by technology

In view of its importance, people have successively developed some effective methods for constructing the structural skeleton of 2-hydroxybenzophenone and 4-hydroxybenzophenone. The synthesis methods of ketones are rarely reported, and these synthesis methods still have problems such as poor regioselectivity, harsh reaction conditions, and low atom economy, which limit their application in actual production.

Method used

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  • Synthesis method of 3'-acyl-2,4'-dihydroxyl diphenyl ketone compound
  • Synthesis method of 3'-acyl-2,4'-dihydroxyl diphenyl ketone compound
  • Synthesis method of 3'-acyl-2,4'-dihydroxyl diphenyl ketone compound

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Embodiment 1

[0011]

[0012] A reaction tube containing 1a (0.3mmol, 52mg), 2a (0.3mmol, 52mg), acetonitrile (2mL) and sulfuric acid aqueous solution (0.15mmol, 4.74M, 32μL) was placed in a 70°C oil bath and stirred for 2h. Then water (3 mL) and potassium carbonate (0.45 mmol, 62 mg) were added, and the reaction tube was placed in an oil bath at 80° C., and stirred for 0.5 h. The reaction was quenched by adding 10 mL of saturated brine, extracted with ethyl acetate (10 mL×3), and the organic phases were combined and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=40 / 1) to obtain product 3a (75 mg, 75%) as a yellow solid. The characterization data of this compound are as follows: 1 H NMR (600MHz, CDCl 3 )δ: 2.73(s, 3H), 6.92(t, J=7.2Hz, 1H), 7.09(d, J=8.4Hz, 1H), 7.38(t, J=7.2Hz, 1H), 7.45(t, J=7.2Hz, 2H), 7.52(t, J=7.2Hz, 1H), 7.59(d, J=7.8Hz, 2H), 7.63(d, J=7.8Hz, 1H), 7.92(d, J= 1.8Hz,1H),8.19(d,J=...

Embodiment 2

[0014] A reaction tube containing 1a (0.3mmol, 52mg), 2a (0.3mmol, 52mg), acetonitrile (2mL) and sulfuric acid aqueous solution (0.15mmol, 4.74M, 32μL) was placed in a 70°C oil bath and stirred for 2h. Then N,N-dimethylformamide (3 mL) and potassium carbonate (0.45 mmol, 62 mg) were added, and the reaction tube was placed in an oil bath at 80° C., and stirred for 0.5 h. The reaction was quenched by adding 10 mL of saturated brine, extracted with ethyl acetate (10 mL×3), and the organic phases were combined and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=40 / 1) to obtain product 3a (57 mg, 57%) as a yellow solid.

Embodiment 3

[0016] A reaction tube containing 1a (0.3mmol, 52mg), 2a (0.3mmol, 52mg), acetonitrile (2mL) and sulfuric acid aqueous solution (0.15mmol, 4.74M, 32μL) was placed in a 70°C oil bath and stirred for 2h. Then tetrahydrofuran (3 mL) and potassium carbonate (0.45 mmol, 62 mg) were added, and the reaction tube was placed in an oil bath at 80° C., and stirred for 0.5 h. The reaction was quenched by adding 10 mL of saturated brine, extracted with ethyl acetate (10 mL×3), and the organic phases were combined and dried over anhydrous sodium sulfate. Filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=40 / 1) to obtain product 3a (60 mg, 60%) as a yellow solid.

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Abstract

The invention discloses a synthesis method of a 3'-acyl-2,4'-dihydroxyl diphenyl ketone compound, and belongs to the technical field of organic synthesis. The key point of the technical scheme of the invention is as follows: the synthesis method of the 3'-acyl-2,4'-dihydroxyl diphenyl ketone compound particularly comprises the following processes: disoolving a 3,4-diene-2-pentanone compound and a 3-formyl chromone compound into a first solvent, performing stirring reaction at a temperature of 50 to 80 DEG C under the acidic condition, adding a second solvent and alkali, and performing stirring reaction at 60 to 100 DEG C to prepare the 3'-acyl-2,4'-dihydroxyl diphenyl ketone compound. The 3'-acyl-2,4'-dihydroxyl diphenyl ketone compound is synthesized through one-pot multi-step cascade reaction of the 3,4-diene-2-pentanone compound and the 3-formyl chromone compound; the synthesis method of the 3'-acyl-2,4'-dihydroxyl diphenyl ketone compound has the advantates of simplicity and convenience in operation, mild condition, wide application range of substrates and the like, and is suitable for industrialized production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 3'-acyl-2,4'-bishydroxybenzophenone compounds. Background technique [0002] 2-Hydroxybenzophenone and 4-Hydroxybenzophenone skeletons are widely found in natural products. In addition, 2-hydroxybenzophenone and 4-hydroxybenzophenone compounds are also key intermediates for the preparation of fine chemicals such as dyes, perfumes and pharmaceuticals. In view of its importance, people have successively developed some effective methods for constructing the structural skeleton of 2-hydroxybenzophenone and 4-hydroxybenzophenone. The synthesis methods of ketones are rarely reported, and these synthesis methods still have problems such as poor regioselectivity, harsh reaction conditions, and low atom economy, which limit their application in actual production. Therefore, it is not only important to study and develop a new method of synthesi...

Claims

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Application Information

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IPC IPC(8): C07C45/60C07C45/79C07C49/83C07C49/84C07D333/22
CPCC07C45/60C07C45/79C07D333/22C07C49/83C07C49/84
Inventor 范学森师晓楠何艳张新迎
Owner HENAN NORMAL UNIV
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