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Synthesis method of p-hydroxy-beta-nitrostyrene

A technology of nitrostyrene and a synthesis method, which is applied in the preparation of nitro compounds, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of easy conversion, poor stability, large product loss, etc., and achieves the reaction cost. Low, simple post-processing, and the effect of improving utilization

Inactive Publication Date: 2014-01-08
ZHONGBEI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Because the solubility of p-hydroxyl-β-nitrostyrene in ethanol is also relatively large at normal temperature, and p-hydroxyl-β-nitrostyrene is less stable in hot ethanol and is prone to conversion, so although the recrystallization method can The product with high purity is obtained, but in the process of heating and dissolving and cooling and recrystallization, the loss of the product is also relatively large

Method used

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  • Synthesis method of p-hydroxy-beta-nitrostyrene
  • Synthesis method of p-hydroxy-beta-nitrostyrene
  • Synthesis method of p-hydroxy-beta-nitrostyrene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Take 10mL of glacial acetic acid, add 0.02g of anhydrous hydroquinone, and let stand for 45 minutes.

[0027] Add 3.66g (0.03mol) of p-hydroxybenzaldehyde, 5.1mL (0.09mol) of nitromethane, the above-mentioned 10mL of glacial acetic acid, and 1g of ammonium acetate into a 250mL three-necked flask equipped with a magnetic stirrer, a thermometer and a reflux condenser, and stir Heated to 120°C for 1 hour, then added 0.39 g of ammonium acetate, and maintained at 120°C for 3 hours.

[0028] Change the reflux device to a distillation device, add 8 mL of toluene, distill the fraction after half an hour, and stop the reaction.

[0029] After the reaction was completed and cooled, the reactant was poured into an appropriate amount of ice water, and a yellow precipitate was precipitated. Without filtering, directly heat the system to 60-70°C, slowly add ethanol dropwise under stirring, until the precipitate is completely dissolved, then pour the solution into an appropriate amou...

Embodiment 2

[0033] Take 20mL of glacial acetic acid, add 0.04g of anhydrous hydroquinone, and let stand for 30 minutes.

[0034] Add 3.66g (0.03mol) of p-hydroxybenzaldehyde, 1.7mL (0.03mol) of nitromethane, the above-mentioned 20mL of glacial acetic acid, and 0.77g of ammonium acetate into a 250mL three-necked flask equipped with a magnetic stirrer, a thermometer and a reflux condenser in sequence, Heat to 80°C for 1 hour under stirring, then add 0.39 g of ammonium acetate, and maintain 80°C for 3 hours.

[0035] Change the reflux device to a distillation device, add 8 mL of toluene, distill the fraction after half an hour, and stop the reaction.

[0036] After the reaction was completed and cooled, the reactant was poured into an appropriate amount of ice water, and a yellow precipitate was precipitated. Without filtering, directly heat the system to 60-70°C, slowly add ethanol dropwise under stirring, until the precipitate is completely dissolved, then pour the solution into an approp...

Embodiment 3

[0039] Take 15mL of glacial acetic acid, add 0.03g of anhydrous hydroquinone, and let stand for 45 minutes.

[0040]Add 3.66g (0.03mol) of p-hydroxybenzaldehyde, 5.1mL (0.09mol) of nitromethane, the above-mentioned 15mL of glacial acetic acid, and 0.26g of ammonium acetate into a 250mL three-necked flask equipped with a magnetic stirrer, a thermometer and a reflux condenser in sequence, Heat to 100°C for 1 hour under stirring, then add 0.12 g of ammonium acetate, and maintain 100°C for 3 hours.

[0041] Change the reflux device to a distillation device, add 6 mL of toluene, distill the distillate after half an hour, and stop the reaction.

[0042] After the reaction was completed and cooled, the reactant was poured into an appropriate amount of ice water, and a yellow precipitate was precipitated. Without filtering, directly heat the system to 60-70°C, slowly add ethanol dropwise under stirring, until the precipitate is completely dissolved, then pour the solution into an app...

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Abstract

The invention discloses a synthesis method of p-hydroxy-beta-nitrostyrene, which comprises the following step: synthesizing p-hydroxybenzaldehyde and nitromethane used as raw materials into p-hydroxy-beta-nitrostyrene by using ammonium acetate as a catalyst and glacial acetic acid as a solvent, wherein an antioxidant anhydrous hydroquinone is added to protect the raw material p-hydroxybenzaldehyde from oxidation, and toluene is added in the later reaction period to take the generated water out of the reaction system, so that the reaction proceeds in the positive reaction direction. The method has the advantages of low reaction cost, high product yield, simple after-treatment and the like, and the yield of the hydroxy-beta-nitrostyrene can reach higher than 92%.

Description

technical field [0001] The invention relates to a method for synthesizing α-aryl-β-nitroethylene compounds, in particular to a method for synthesizing p-hydroxyl-β-nitrostyrene. Background technique [0002] α-aryl-β-nitroethylene compounds not only have obvious bactericidal and antitumor activities, but also are widely used organic synthesis intermediates. This is due to the strong electron-withdrawing properties of the nitro group, which makes nitroethylene have obvious electron-deficient characteristics and is easily attacked by nucleophiles, making it a good dienophile. Through different methods, the nitro group in α-aryl-β-nitrovinyl compounds can be converted into a variety of functional groups, thereby forming different functional groups such as amine, oxime, hydroxyl, nitrile, aldehyde, alcohol, ketone, heterocycle, etc. types of compounds. [0003] p-hydroxy-β-nitrostyrene (p-hydroxy-β-nitrostyrene) is a representative substance of α-aryl-β-nitroethylene compounds...

Claims

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Application Information

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IPC IPC(8): C07C205/17C07C201/06C07C201/16
Inventor 崔建兰王立敏邓德志赵林秀
Owner ZHONGBEI UNIV
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