Synthesizing method of propiophenone compound

A synthesis method and compound technology are applied in the synthesis field of propiophenone compounds, which can solve problems such as complicated reaction steps, and achieve the effects of reducing reaction cost, simplifying synthesis route and simple operation.

Active Publication Date: 2016-06-08
吉林中科研伸科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] But no matter which of the above synthetic routes, organic solvents other than tert-butyl hydroperoxide will be used in the reaction, and

Method used

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  • Synthesizing method of propiophenone compound
  • Synthesizing method of propiophenone compound
  • Synthesizing method of propiophenone compound

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preparation example Construction

[0018] The embodiment of the present invention provides a synthetic method of propiophenone compounds, comprising:

[0019] S1: Add propylbenzene, organic acid, iodine, and tert-butyl hydroperoxide into the reaction kettle, and react at 80°C-120°C for 8-24 hours.

[0020] In this step, the "one-pot method" can be used to synthesize propiophenone compounds. Specifically, propylbenzene, organic acid, tert-butyl hydroperoxide and iodine are added to the reaction kettle together, and heated at 80°C- React at 120°C for 8-24 hours to produce the target product. The specific reaction process is as follows:

[0021]

[0022] S2: After the reaction is completed, the reaction solution is extracted with an organic solvent, and dried to obtain a propiophenone compound:

[0023]

[0024] The embodiment of the present invention provides a kind of synthetic method of propiophenone compound, compared with prior art, the synthetic method provided by the present invention is to utilize p...

Embodiment 1

[0033] Add propylbenzene, acetic acid, iodine, and tert-butyl hydroperoxide with a mmol ratio of 1:1:0.2:6 into the reaction kettle, and react at 80°C for 8 hours; after the reaction is completed, use ethyl acetate The reaction solution was extracted and dried to obtain a colorless oily liquid that is Propiophenone Compound A:

[0034]

[0035] The above-mentioned colorless oily liquid is subjected to nuclear magnetic spectrum analysis, and the data are as follows:

[0036] 1 HNMR (CDCl 3 ,400MHz)δ1.56(d,J=6.8Hz,3H), 2.17(s,3H), 5.99(q,J=6.8Hz,1H), 7.49–7.54(m,2H), 7.60–7.63(m ,1H), 7.95–7.97(m,2H);

[0037] 13 CNMR (CDCl 3 ,100MHz) δ17.2, 20.5, 71.1, 128.2, 128.6, 133.7, 134.5, 170.4, 196.9;

[0038] After identification, the spectral data corresponded to the structural formula, proving that the synthesized compound was propiophenone compound A with a yield of 60%.

Embodiment 2

[0040] Add propylbenzene, isobutyric acid, iodine, and tert-butyl hydroperoxide with a mmol ratio of 1:2:0.3:8 into the reaction kettle, and react at 120°C for 24 hours; after the reaction is completed, use acetic acid The reaction solution was extracted with ethyl ester and dried to obtain a colorless oily liquid, i.e. propiophenone compound B:

[0041]

[0042] Carry out nuclear magnetic spectrum analysis to above-mentioned colorless oily liquid, the data are as follows:

[0043] 1 HNMR (CDCl 3,300MHz) δ1.19-1.20(m,6H), 1.55(q,J=6.9Hz,3H), 2.65(hept,J=6.9Hz,1H), 5.97(q,J=6.9Hz,1H), 7.44-7.53(m,2H), 7.58-7.63(m,1H), 7.93-7.98(m,2H);

[0044] 13 CNMR (CDCl 3 ,75MHz) δ17.1, 18.7, 18.9, 33.9, 71.1, 128.4, 128.7, 133.6, 134.5, 176.8, 197.3;

[0045] After identification, the spectral data corresponded to the structural formula, proving that the synthesized compound was propiophenone compound B with a yield of 69%.

[0046] As can be seen from the foregoing examples, the...

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Abstract

The invention provides a synthesizing method of a propiophenone compound, and belongs to the technical field of organic synthesizing. The synthesizing method has the advantages that the reaction steps for synthesizing the propiophenone compound can be simplified, and the reaction cost is reduced. The synthesizing method of the propiophenone compound comprises the following steps of adding propylbenzene, organic acid, iodine and tert-butyl hydroperoxide into a reaction kettle, and reacting for 8-24h at the temperature of 80-120 DEG C; after the reaction is finished, extracting a reaction solution by an organic solvent, and drying, so as to obtain the propiophenone compound. The synthesizing method can be used for the synthesizing and preparation of the propiophenone compound.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a synthesis method of propiophenone compounds. Background technique [0002] Propiophenone compounds are important intermediates in organic synthesis, widely exist in natural products and pharmaceutical active molecules, and are widely used in chemical production such as medicine and pesticide. [0003] In the synthesis of existing propiophenone compounds, it is often synthesized by using propiophenone as a raw material, for example, it is recorded in Angew. Ammonium iodide, ethyl acetate, and a temperature of 75°C react with organic acids and tert-butyl hydroperoxide to generate propiophenone compounds. In the reaction process, in order to obtain the target product, halides such as tetrabutylammonium iodide are added in the reaction. Of course, halogens can also be added directly, but in this case, it is necessary to add phase transfer catalyst. [0004] But no matt...

Claims

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Application Information

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IPC IPC(8): C07C69/157C07C69/24C07C67/035
CPCC07C67/035C07C69/157C07C69/24
Inventor 董道青王祖利
Owner 吉林中科研伸科技有限公司
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