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Synthetic method of ketone compounds

The technology of a ketone compound and a synthesis method, which is applied in the field of synthesis of ketone compounds, can solve the problems of difficult synthesis of active intermediates, expensive catalysts, cumbersome synthesis steps, etc., and achieve high synthesis efficiency, simple preparation method, and low cost. Effect

Active Publication Date: 2018-10-26
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] In view of this, the present invention provides a synthesis method of ketone compounds, which is used to solve the technical defects of cumbersome synthesis steps, expensive catalysts and difficult synthesis of active intermediates in the synthesis of ketone compounds in the prior art.

Method used

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  • Synthetic method of ketone compounds
  • Synthetic method of ketone compounds
  • Synthetic method of ketone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] This example is the specific preparation method and structural analysis of 4-methoxybenzophenone (3aa).

[0044]

[0045]Under an atmosphere of oxygen or air at atmospheric pressure, p-methoxyphenylhydrazine compound 1a (27.6mg, 0.20mmol), carboformic acid 2a (30mg, 0.20mmol), silver acetate (3.5mg, 0.02 mmol), lithium carbonate (15mg, 0.20mmol), 1,2-dichloroethane (DCE, 1mL), react at a temperature of 110°C for 12 hours.

[0046] 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 the prepared silica gel plate, and the selected developer or eluent was petroleum ether and ethyl acetate at a volume ratio of 100:1 to obtain the product 4-methoxybenzophenone 3aa. The yield was 82% (34.8 mg).

[0047] 1 H-NMR (400MHz, CDCl 3 )δ7.84-7.81(m,2H),7.76-7.74(m,1H),7.56(t,J=3.2Hz,1H),7.46(t,J=7.6Hz,2H),6.97-6.94(m ,2H), 3.88...

Embodiment 2

[0050] This example is the specific preparation method and structural analysis of 4-methyl-4'-trifluoromethyl-benzophenone (3bb).

[0051]

[0052] Under an atmosphere of oxygen at atmospheric pressure, p-methoxyphenylhydrazine compound 1b (24.4mg, 0.20mmol), carboformic acid 2b (64.8mg, 0.30mmol), silver acetate (3.5mg, 0.02mmol) were successively added to a 15mL Schlenk reaction tube ), lithium carbonate (15mg, 0.20mmol), 1,2-dichloroethane (DCE, 1mL), react at a temperature of 110°C for 12 hours.

[0053] 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 the prepared silica gel plate, and the selected developer or eluent was petroleum ether and ethyl acetate at a volume ratio of 50:1 to obtain the product 4-methyl-4'-trifluoromethyl- Benzophenone 3bb, yield 75% (39.6mg).

[0054] 1 H-NMR (400MHz, CDCl 3 ) δ 7.88 (d, ...

Embodiment 3

[0057] This example is the specific preparation method and structural analysis of 4-chloro-4'-tert-butyl-benzophenone (3cc).

[0058]

[0059] Under an atmosphere of oxygen or air at atmospheric pressure, p-methoxyphenylhydrazine compound 1c (28.4mg, 0.20mmol), carboformic acid 2c (60.4mg, 0.30mmol), silver acetate (3.5mg, 0.02mmol), lithium carbonate (15mg, 0.20mmol), 1,2-dichloroethane (DCE, 1mL), react at a temperature of 110°C for 12 hours.

[0060] 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 the prepared silica gel plate, and the selected developing solvent or eluent was petroleum ether and ethyl acetate at a volume ratio of 100:1 to obtain the product 4-chloro-4'-tert-butyl-diphenyl Methanone 3cc, yield 76% (41.3mg).

[0061] 1 H-NMR (400MHz, CDCl 3 ) δ7.77-7.72 (m, 4H), 7.51-7.49 (m, 2H), 7.46-7.44 (m, 2H),...

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Abstract

The invention belongs to the field of organic synthesis, and particularly relates to a synthetic method of ketone compounds. The invention provides a synthetic method of the ketone compounds. In the presence of a silver catalyst and alkaline additive, hydrazine and carbonyl carboxylic acid are used as substrates to have oxidation reaction to generate the ketone compounds. In the synthetic method of the invention, the used substrates, catalyst and additive are easy to obtain, and the cost is low; meanwhile, the generated byproducts are nitrogen, water and carbon dioxide, so that the synthetic method is environmentally friendly, pollution-free, and capable of meeting the sustainable development concept; and thirdly, by adopting the preparation method, the pre-activation is not needed, the yield is greater than 60 percent or, and the synthetic efficiency is high; and the technical defects in the prior art that the synthesis method of the ketone compounds is complicated in synthetic procedures, high in catalyst price and difficult in synthesizing an active intermediate can be solved.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing ketone compounds. Background technique [0002] Carbonyl compounds play an important role in organic synthesis and are widely used in natural products, drugs, materials, etc. Carbonyl compounds are almost ubiquitous. In terms of organic synthesis, carbonyl compounds are lively, have multiple active reaction sites, and can undergo nucleophilic addition reactions, including: metal organic reagents to synthesize multi-substituted alcohols, Wittig reactions to synthesize olefin compounds, and α- Hydrogen carbonyl compounds can also undergo various Aldol reactions and condensation reactions to obtain various multifunctional carbonyl compounds, which provide key intermediates for subsequent conversion into heterocyclic molecules; others such as Mannich reaction, Perkin reaction, Knoevenagel reaction, Carnnizzarro Reactions, etc. all illustrate the importance ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B37/04C07C45/68C07C49/84C07C49/813C07C49/76C07D333/22C07C67/343C07C69/738
CPCC07B37/04C07B2200/07C07C45/68C07C49/76C07C49/813C07C49/84C07C67/343C07C69/738C07D333/22
Inventor 李先纬饶建行霍延平
Owner GUANGDONG UNIV OF TECH
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