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A green and efficient synthesis method of aryl acrylonitrile compounds

A technology of arylacrylonitrile and synthesis method, which is applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry and other directions, can solve problems such as pollution of the environment and a large amount of alkaline waste water, achieve good purity, reduce production costs, and reduce The effect of pollution

Active Publication Date: 2020-08-21
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional synthesis method of aryl acrylonitrile compound is formed by condensation and dehydration of aromatic aldehyde and cyanoacetate under alkaline conditions. Post-treatment produces a large amount of alkaline wastewater, which seriously pollutes the environment

Method used

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  • A green and efficient synthesis method of aryl acrylonitrile compounds
  • A green and efficient synthesis method of aryl acrylonitrile compounds
  • A green and efficient synthesis method of aryl acrylonitrile compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: the preparation of acrylonitrile compound III-1

[0029] The reaction formula is as follows:

[0030]

[0031] Add 2.344g (20mmol) of phenylacetonitrile I-1, 0.2g (5‰mmol Ru) Ru / C catalyst and 9.910g (100mmol) of methyl cyanoacetate II to the reaction flask, and stir the reaction at 160°C under air atmosphere After 4 hours, it was detected by TLC that the reaction of benzyl nitrile was complete, and the reaction was stopped. The reaction was cooled to room temperature, the Ru / C catalyst was recovered by filtration, and the filtrate was distilled under reduced pressure at 10 mmHg (collecting fractions with a boiling point of 82°C to 84°C) to recover methyl cyanoacetate II for the next batch of reactions. 15 mL of ethanol was added to the distillation residue for recrystallization, and finally 3.668 g of solid was obtained by filtration, with a yield of 98.0% and a purity of 99.0%. The filtrate was evaporated by a rotary evaporator to recover ethanol for...

Embodiment 2

[0033] Embodiment 2: the preparation of acrylonitrile compound III-2

[0034] The reaction formula is as follows:

[0035]

[0036] Add 2.624g (20mmol) of o-tolueneacetonitrile I-2, 0.2g (5‰mmol Ru) Ru / C catalyst and 9.910g (100mmol) of methyl cyanoacetate II in the reaction flask, the following operations are implemented with example 1. Finally, 3.896 g of solid was obtained by filtration, with a yield of 96.8% and a purity of 99.0%. The filtrate was evaporated by a rotary evaporator to recover ethanol, which was used for the next batch of reactions. The structural representation of compound formula III-2 is as follows:

[0037] 1 H-NMR (CDCl 3 ,500MHz): δ8.54(s,1H),8.12(d,J=4.0Hz,2H),7.40-7.24(m,3H),3.91(s,3H),2.41(s,3H); 13 C-NMR (CDCl 3 ,125MHz): δ162.7,153.2,139.6,132.7,130,9,130,3,128.4,126.5,115.1,103.9,53.2,19.6; GC-MS(EI):m / z 201[M + ].

Embodiment 3

[0038] Embodiment 3: the preparation of acrylonitrile compound III-3

[0039] The reaction formula is as follows:

[0040]

[0041] In the reaction flask, add 2.624g (20mmol) of p-toluene acetonitrile I-3, 0.4g (10‰mmol Ru) Ru / C catalyst and 9.910g (100mmol) of methyl cyanoacetate II, under air atmosphere 160 The reaction was stirred at °C for 3 h, and the following operations were the same as in Example 1. Finally, 3.976 g of solids were obtained by filtration, with a yield of 98.8% and a purity of 99.0%. The filtrate was evaporated by a rotary evaporator to recover ethanol for use in the next batch of reactions. The structural representation of compound formula III-3 is as follows:

[0042] 1H-NMR (CDCl 3 ,500MHz):δ8.21(s,1H),8.89(d,J=8.0Hz,2H),7.29(d,J=8.0Hz,2H),3.92(s,3H),2.43(s,3H) ; 13 C-NMR (CDCl 3 ,125MHz): δ163.2,155.2,144.8,131.3,130.0,128.8,115.7,101.1,53.3,21.8; GC-MS(EI):m / z201[M + ].

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Abstract

The invention discloses a green and efficient synthesis method for an aryl acrylonitrile compound represented by formula III. The method comprises the following steps: in an air atmosphere, by takingaryl acetonitrile of formula I as shown in the specification and excess methyl cyanoacetate of formula II as shown in the specification as raw materials, and Ru / C as a catalyst, enabling the components to react at 150-160 DEG C in the absence of a solvent, and separating and purifying a reaction mixture obtained after the reaction is completed, thereby obtaining an aryl acrylonitrile compound of formula III as shown in the specification. The method disclosed by the invention is not only low in production cost, but also good in environment protection, and is very applicable to industrial large-scale production.

Description

technical field [0001] The present invention relates to a kind of synthetic method of the aryl acrylonitrile compound shown in formula III, [0002] Background technique [0003] Acrylonitrile compounds are an important class of bulk chemical intermediates, among which acrylonitrile compounds have a unique structure, a novel mechanism of action and high biological activity, and are environmentally friendly, and are widely used in chemical industry, materials, medicine, pesticides and other industries. For example, Cao Youqin et al. (1988, Cao Youqin et al.) reported the fungicide (suppression) effect of cinnamon nitrile, and it found that cinnamon nitrile is effective against various molds, including common molds in grain, vegetables and fruits, such as Rhizopus stolonifer, Rhizopus stolonifer, Alternaria tenuis, Penicillum chrysogenum, Penicillumnototum, etc. and human potential molds all have good bactericidal (inhibitory) effects. In 2003, Toru et al published a seri...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C253/30C07C255/41C07D333/24
CPCC07C253/30C07D333/24C07C255/41
Inventor 王宇光朱冰春张程
Owner ZHEJIANG UNIV OF TECH
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