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A kind of preparation method and application of 3-phenyl-2-propen-1-one o-n-butyl oxime

A technology of n-butyl oxime and phenyl, which is applied in the field of organic synthesis, can solve the problems of strong toxicity and unsuitability for large-scale production, and achieve the effects of convenient operation, low energy consumption, and reduced production costs

Active Publication Date: 2022-06-28
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Zhukovskaya, N.A. [3] et al. use benzene as a solvent and perchloric acid as a catalyst. One is that benzene is a solvent, which is too toxic; the other is that perchloric acid is a super acid, which has high requirements for production equipment and operation, so this method is not suitable for large-scale Production

Method used

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  • A kind of preparation method and application of 3-phenyl-2-propen-1-one o-n-butyl oxime
  • A kind of preparation method and application of 3-phenyl-2-propen-1-one o-n-butyl oxime
  • A kind of preparation method and application of 3-phenyl-2-propen-1-one o-n-butyl oxime

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] A magnetic stirring bar was added to a 100mL single-necked flask, and 1.32g (0.01mol) of cinnamaldehyde, 0.86g (0.0125mol) of hydroxylamine hydrochloride, 1.37g (0.01mol) of bromobutane, and 5g of potassium hydroxide were added to the round-bottomed flask, Add 2 mL of ethanol, H 2 O5mL, the temperature was raised to 80°C and the reaction was stirred for 5 hours. After the completion of the reaction, the reaction was carried out under reduced pressure for precipitation, and flash column chromatography was performed using petroleum ether and ethyl acetate (50:1) to obtain 3-phenyl-2-propen-1-one O-n-butyl oxime, which was pale Yellow oily liquid (yield: 78%). The NMR results of the compounds are figure 1 , figure 2 shown.

[0038] compound 1 H-NMR (600MHz, DMSO) δ: 7.99 (d, J=9.3 Hz, 1H), 7.56 (d, J=7.5 Hz, 2H), 7.38 (t, J=7.5 Hz, 2H), 7.32 (t, J=7.3Hz, 1H), 6.93(dt, J=16.0, 12.7Hz, 2H), 4.04(t, J=6.6Hz, 2H), 1.64(m, 2H), 1.40(m, 2H), 0.91( t, J=7.4 Hz, 3H), M / z: ...

Embodiment 2

[0040] A magnetic stirring bar was added to the 100mL single-necked flask, and 1.32g (0.01mol) of cinnamaldehyde, 0.86g (0.0125mol) of hydroxylamine hydrochloride, 1.51g (0.011mol) of bromo-n-butane, and 5g of potassium hydroxide were added to the round-bottomed flask, Add 2 mL of ethanol, H 2O 5mL, the temperature was raised to 80°C and the reaction was stirred for 5 hours. After the completion of the reaction, it was desolvated under reduced pressure, and flash column chromatography was performed using petroleum ether and ethyl acetate (50:1) to obtain 3-phenyl-2-propen-1-one O-n-butyl oxime, which was pale Yellow oily liquid (yield: 82%).

Embodiment 3

[0042] A magnetic stirring bar was added to a 100mL single-necked flask, and 1.32g (0.01mol) of cinnamaldehyde, 0.86g (0.0125mol) of hydroxylamine hydrochloride, 1.71g (0.0125mol) of bromo-n-butane, and 5g of potassium hydroxide were added to the round-bottomed flask, Add 2 mL of ethanol, H 2 O 5mL, the temperature was raised to 80°C and the reaction was stirred for 5 hours. After the completion of the reaction, it was desolvated under reduced pressure, and flash column chromatography was performed using petroleum ether and ethyl acetate (50:1) to obtain 3-phenyl-2-propen-1-one O-n-butyl oxime, which was pale Yellow oily liquid (yield: 92%).

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Abstract

A 3‑phenyl‑2‑propen‑1‑one O A preparation method for n-butyl oxime, which belongs to the technical field of organic synthesis. The method uses 3-phenyl-2-acrolein, hydroxylamine hydrochloride and brominated n-butane as raw materials, and is prepared under potassium hydroxide alkaline conditions. The crude product obtained from the reaction obtains 3-phenyl-2-propene-1-ketone through flash column chromatography O ‑n-Butyl oxime. Compound 3‑phenyl‑2‑propen‑1‑one O ‑n-Butyl oxime can be used as a new type of polymerization inhibitor, especially for styrene. Adopt method of the present invention to prepare 3-phenyl-2-propene-1-ketone under conventional conditions O ‑n-Butyl oxime, safe and simple to operate, saving energy. The starting material of the method is cheap, which is beneficial to reduce the production cost. The process is simple, the operation is convenient, and the conversion rate of raw materials is high.

Description

technical field [0001] The invention relates to a method for synthesizing O-n-butyl oxime compounds, in particular to a method for preparing 3-phenyl-2-propen-1-one O-n-butyl oxime, which belongs to the technical field of organic synthesis. Background technique [0002] 3-Phenyl-2-propen-1-one O-n-butyl oxime, its molecular formula is C 13 H 17 NO, whose chemical formula is shown in formula S-1; is an O-n-butyl oxime compound. [0003] [0004] 3-Phenyl-2-propen-1-one O-n-butyl oxime can be used as a new type of polymerization inhibitor, especially it has a good inhibitory effect on styrene. At present, there is no literature report about 3-phenyl-2-propen-1-one O-n-butyl oxime and its synthesis method. [0005] By consulting the literature, found its analogs, acetophenone O-n-butyl oxime, 3-phenyl-2-propen-1-one O-methyl oxime, 3-phenyl-2-propen-1-one O The preparation methods of benzyl oxime and 3-phenyl-2-propen-1-one O(1-oxybutyl) oxime mainly include the followin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C251/40C07C249/04C07C249/14C07C7/20C07C15/46
CPCC07C249/04C07C249/14C07C7/20C07C251/40C07C15/46
Inventor 高欣钦安孔雪张硕齐哲铖
Owner DALIAN UNIV OF TECH
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