1-aryl-2-acetone compound preparation method

A compound, aryl acrylic acid technology, applied in the field of 1-aryl-2-acetone compound synthesis, can solve the problems of high explosiveness, complicated operation, long steps, etc., and achieves reduction of reaction steps, improved operation safety, operation The effect of process coherence

Pending Publication Date: 2019-12-20
ZHEJIANG PHARMA COLLEGE
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] Purpose of the invention: In order to solve the problem in the prior art of using unavailable, highly corrosive, highly toxic and highly explosive reagents in the process of synthesizing 1-aryl-2-acetone, and the steps are long, the yield is low, and the operation is cumbersome, etc. Technical problem, the present invention provides a kind of preparation method of 1-aryl-2-acetone compound, and this method raw material is easy to obtain, and operation is safe and simple, and condition is mild, and yield is high, is suitable for industrialized production

Method used

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Experimental program
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Effect test

Embodiment 1

[0038] 30.0g (184.97mmol) of (E)-2-methyl-3-phenylacrylic acid, 200mL of toluene, 51.9g (188.67mmol) of DPPA and 19.6g (194.22mmol) of triethylamine were successively added to a 500mL reaction flask, The reaction was stirred at 25 °C for 30 min; the temperature was raised to 110 °C for 1 h; 100 mL of concentrated hydrochloric acid was added to the reaction solution, and the reaction was continued for 1 h. The reaction solution was cooled to room temperature, the organic layer was separated, the organic layer was washed with saturated sodium carbonate solution, and the toluene was evaporated under reduced pressure to obtain a yellow oily liquid. . The product is analyzed by gas chromatography, and the purity is over 99.5%. 1H NMR (CDCl 3, 300MHz): δ (ppm) 7.22-7.39 (m, 5H), 3.71 (s, 2H), 2.17 (s, 3H); 13C NMR (CDCl 3 , 101MHz): δ (ppm) 206.3, 134.3, 129.4, 128.8, 127.1, 51.0, 29.3; GC-MS (EI) found 134.2 [M + ].

Embodiment 2

[0040] (E)-2-methyl-3-(4-methoxyphenyl)acrylic acid 30.0 g (156.08 mmol), toluene 200 mL, DPPA 43.8 g (159.20 mmol) and triethylamine 16.6 g (163.88 mmol) were sequentially It was added to a 500 mL reaction flask, and the reaction was stirred at 25 °C for 30 min; the temperature was raised to 110 °C for 1.5 h; 100 mL of concentrated hydrochloric acid was added to the reaction solution, and the reaction was continued for 1 h. The reaction solution was cooled to room temperature, the organic layer was separated, the organic layer was washed with saturated sodium carbonate solution, and the toluene was evaporated under reduced pressure to obtain a yellow oily liquid. The crude product was rectified to obtain 1-(4-methoxyphenyl)-2-propanone 21.8g, 85% yield. The product is analyzed by gas chromatography, and the purity is over 99.5%. GC-MS(EI) found 164.1[M + ].

Embodiment 3

[0042] (E)-2-methyl-3-(3,4-dimethoxyphenyl)acrylic acid 30.0 g (134.99 mmol), toluene 200 mL, DPPA 37.9 g (137.69 mmol) and triethylamine 14.3 g (141.74 mmol) mmol) were sequentially added to a 500 mL reaction flask, and the reaction was stirred at 25 °C for 1 h; the temperature was raised to 110 °C for 1.5 h; 100 mL of concentrated hydrochloric acid was added to the reaction solution, and the reaction was continued for 1.5 h. The reaction solution was cooled to room temperature, the organic layer was separated, the organic layer was washed with saturated sodium carbonate solution, and the toluene was evaporated under reduced pressure to obtain a yellow oily liquid. The crude product was rectified to obtain 1-(4-methoxyphenyl)-2-propanone 21.5g, yield 82%. The product is analyzed by gas chromatography, and the purity is over 99.5%. GC-MS(EI)found 194.1[M + ].

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Abstract

The invention discloses a 1-aryl-2-acetone compound preparation method, which comprises: (1) carrying out a reaction on (E)-2-methyl-3-aryl acrylic acid (I) as a starting raw material and diphenyl azidophosphate (DPPPA) in the presence of an organic alkali; (2) carrying out a heating reaction; and (3) adding an acidic aqueous solution into the reaction solution, and carrying out a reaction to obtain the 1-aryl-2-acetone compound with a structural formula (IV). According to the present invention, the method can solve the technical problems of difficultly available, highly-corrosive, highly toxic and highly explosive reagents, long steps, low yield, tedious operation and the like in the 1-aryl-2-acetone synthesis in the prior art, has characteristics of easily available raw materials, safe and simple operation, mild condition and high yield, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of 1-aryl-2-acetone compounds, and belongs to the technical field of 1-aryl-2-acetone compound synthesis. Background technique [0002] 1-Aryl-2-propanone is an important pharmaceutical and chemical intermediate, which is widely used in the pharmaceutical field. For example, 1-(4-methoxyphenyl)-2-propanone is a drug for the treatment of chronic bronchial asthma. Luo's important intermediates; 1-(3,4-dimethoxyphenyl)-2-propanone and 1-(3,4-methylenedioxyphenyl)-2-propanone are antihypertensive drugs The main raw material of gidopa; 1-(2-methoxyphenyl)-2-propanone is the key intermediate of methoxyphenamine hydrochloride, a drug for the treatment of bronchial asthma; 1-phenyl-2-propanone can be used to synthesize hydrochloric acid Selegiline in the treatment of Parkinson's syndrome can also be used to synthesize anti-angina drugs such as cardiodine lactate. [0003] So far, a variety of methods for synthesi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/213C07C45/00C07C49/255C07C201/12C07C205/45C07C49/233
CPCC07C49/213C07C49/255C07C205/45C07C49/233
Inventor 贾姝姚晓敏陈磊
Owner ZHEJIANG PHARMA COLLEGE
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