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Synthesis method of 4-nitrobenzene ethane

A synthetic method, the technology of nitroethylbenzene, which is applied in the field of synthesis of 4-nitroethylbenzene, can solve the problems of no ortho-para selectivity, unsatisfactory yield, high price, etc.

Pending Publication Date: 2022-05-27
NANTONG UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Method 2: see Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1988, vol.37, #3, p.612–614, mix ethylbenzene, potassium nitrate and trifluoroacetic acid Uniform, heated to 50 ° C, reacted for 0.5 hours, finally obtained 4-nitroethylbenzene with a yield of 48% and 2-nitroethylbenzene with a yield of 49% (molar ratio close to 1:1), this method avoids strong acid Nitric acid and concentrated sulfuric acid system, the reaction speed is fast, but this method still has no ortho-para selectivity, even if the raw material trifluoroacetic acid is recovered and used mechanically, the price is expensive, the yield is not satisfactory, and it is not suitable for industrial production. The synthetic route is:

Method used

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  • Synthesis method of 4-nitrobenzene ethane
  • Synthesis method of 4-nitrobenzene ethane
  • Synthesis method of 4-nitrobenzene ethane

Examples

Experimental program
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Embodiment 1

[0025] Ethylbenzene (106.2 g, 1mol) was dissolved in nitromethane (150ml), stirred, and the fumetic acid (63g, 1.0mol) and urea (0.3 g, 0.005mol) were added dropwise, respectively, the reaction temperature was controlled at 45 °C, the reaction was 2.0 hours, and the product was nuclear magnetic resonance hydrogen spectrogram as shown Figure 1 As shown, 148 °C distillation collected product 4-nitroethylbenzene 111.9g, yield 74%, distillation to recover the solvent nitromethane.

[0026] Figure 1 In the middle, the integration height shows 2-nitroethylbenzene: 4-nitroethylbenzene = 1:3.72, showing good reaction selectivity, and the arrows on the figure indicate the chemical displacement and integration of ethyl, Figure 1 Description, the present invention provides a method product of only a very small amount of dinitroethylbenzene generated, indicating that the synthesis method of the present invention is very selective, the target 4- nitroethylbenzene is the dominant product.

[0...

Embodiment 2

[0029] Ethylbenzene (106.2 g, 1mol) was dissolved in acetic acid (90ml), stirred, and the fuming nitric acid (63g, 1mol) and potassium nitrate (0.425 g, 0.005 mol) were added dropwise, the reaction temperature was controlled at 40 °C, the reaction was 2.5 hours, the solvent acetic acid was recovered by distillation, and the collection product 4-nitroethylbenzene was distilled at 148 °C at 90.7 g, with a yield of 60%.

Embodiment 3

[0031] Ethylbenzene (106.2 g, 1mol) was dissolved in acetic acid (85ml), stirred, and smoked nitric acid (63g, 1mol) and urea (0.425 g, 0.005 mol) were added dropwise, respectively, the reaction temperature was controlled at 40 °C, the reaction was 2.5 hours, the solvent acetic acid was recovered by distillation, and the collection product 4-nitroethylbenzene 105.8g was distilled at 148 °C, with a molar yield of 70%.

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Abstract

The invention belongs to the field of organic synthesis, and discloses a synthesis method of 4-nitroethylbenzene. The synthetic method specifically comprises the following step: reacting ethylbenzene with nitric acid in the presence of an organic solvent and a catalyst to obtain 4-nitroethylbenzene. The method is low in raw material price, high in reaction selectivity, low in reaction equipment requirement and investment, few in three wastes and environment-friendly, the reaction solvent is recycled and reused, and the obtained product is few in isomer, high in conversion rate and yield and high in product purity.

Description

Technical field [0001] The present invention belongs to the field of organic synthesis, particularly relates to a synthesis method of 4-nitroethylbenzene. Background [0002] The structural formula of 4-nitroethylbenzene is: It is a very important basic chemical raw material and the starting material for the classic synthesis of chloramphenicol. [0003] Chloramphenicol antibiotics can act on the 50S subunit of the bacterial ribonucleoproteosome, hinder protein synthesis, and are bacteriostatic broad-spectrum antibiotics. Chloramphenicol has an inhibitory effect on both gram-positive and gram-negative bacteria, and has a strong effect on the latter. Among them, the effect on typhoid bacillus, influenza bacillus, parainfluenza and pertussis bacillus is stronger than other antibiotics, and it is also effective for lyclamider infections such as typhus. The antibacterial mechanism of action is to bind to the nucleoproteosome 50S subunit, inhibit peptide acyltransferase, thereby inhi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/08C07C205/06
CPCC07C201/08C07C205/06Y02P20/584
Inventor 刘伟曾翼陆洋沈浩亮包玉华
Owner NANTONG UNIVERSITY
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