Green and efficient synthesis method for aryl acrylonitrile compound
An arylacrylonitrile technology and a synthesis method are applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., and can solve problems such as a large number of alkaline waste water and environmental pollution, and achieve reduced production costs, good purity, and reduced production costs. The effect of pollution
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Embodiment 1
[0028] Example 1: Preparation of acrylonitrile compound III-1
[0029] The reaction formula is as follows:
[0030]
[0031] Add 2.344g (20mmol) of benzylacetonitrile I-1, 0.2g (5‰mmol Ru) Ru / C catalyst and 9.910g (100mmol) of methyl cyanoacetate II into the reaction flask, and stir the reaction at 160°C under air atmosphere 4h, using TLC method to detect the complete reaction of benzyl cyanide, stop the reaction. 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 the fractions with a boiling point of 82°C to 84°C) to recover methyl cyanoacetate II for use in 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 filtered, with a yield of 98.0% 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 s...
Embodiment 2
[0033] Example 2: Preparation of acrylonitrile compound III-2
[0034] The reaction formula is as follows:
[0035]
[0036] Add 2.624g (20mmol) o-tolueneacetonitrile I-2, 0.2g (5‰mmol Ru) Ru / C catalyst and 9.910g (100mmol) methyl cyanoacetate II into the reaction flask, and the following operations are the same 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 for use in the next batch of reactions. The structure of compound III-2 is characterized 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] Example 3: Preparation of acrylonitrile compound III-3
[0039] The reaction formula is as follows:
[0040]
[0041] 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 into the reaction flask, 160 under air atmosphere The reaction was stirred at °C for 3h, and the following operations were the same as in Example 1. Finally, 3.976 g of solid was 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 structure of compound formula III-3 is characterized as follows:
[0042] 1 H-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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