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Synthesis method of 2-hydroxyl-3-nitroacetophenone

A technology for the synthesis of nitroacetophenone, which is applied in the field of preparation of organic intermediates, can solve the problems of tediousness, few synthesis methods, and low yield, and achieve the effects of reducing waste discharge, reducing costs, and easily obtaining raw materials

Active Publication Date: 2017-03-29
湖北相和精密化学有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There are not many synthetic methods of 2-hydroxyl-3-nitroacetophenone according to literature records, and it is easy for professionals to think of using 2-hydroxylacetophenone to obtain 2-hydroxyl-3-nitroacetophenone and 2-nitroacetophenone through nitration. Hydroxy-5-nitroacetophenone mixture, and then separated to obtain 2-hydroxy-3-nitroacetophenone, but the separation of the mixture is not only time-consuming and cumbersome when made according to the above method, the yield is low, and the cost is also high
The unsatisfactory by-product 2-hydroxy-5-nitroacetophenone has no use, and it takes manpower and material resources to deal with it, resulting in a certain waste of cost

Method used

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  • Synthesis method of 2-hydroxyl-3-nitroacetophenone
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  • Synthesis method of 2-hydroxyl-3-nitroacetophenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The first step: ethyl esterification reaction

[0032] Put 0.1 mol of p-tert-butylphenol, 0.105 mol of acetyl chloride and 50ml of chloroform into the reaction flask, reflux at 60-70°C for 5 hours, and monitor the conversion rate of 99% by HPLC. Without treatment, it was directly transferred to the second step reaction.

[0033] Step 2: Fries rearrangement reaction

[0034] Add 0.105 moles of aluminum trichloride to the reaction liquid in the first step, continue to reflux, control the temperature at 60-70 degrees, monitor the reaction by HPLC, and the conversion rate reaches more than 99% after 5 hours. The reaction was stopped, poured into 100 g of ice water for hydrolysis, allowed to stand for stratification, and the organic layer was directly transferred to the next reaction.

[0035] The third step: nitrification reaction

[0036] Put the organic layer of the second step into the reaction bottle, lower the temperature to 10 degrees, then drop 33.1 g (0.105 mol) ...

Embodiment 2

[0040] The first step: ethyl esterification reaction, put 0.1 mole of p-tert-butylphenol, 0.11 mole of acetic anhydride and 50ml of chloroform into the reaction bottle, reflux at 60-70 degrees for 6 hours, and the reaction conversion rate is 99.5% monitored by HPLC. The reaction solution was decompressed at 900C to steam low boilers, and then transferred to the second step reaction.

[0041] Step 2: Fries rearrangement reaction

[0042] Add 50ml of chloroform and 0.12 moles of ferric chloride to the first step reaction solution, continue to reflux, control the temperature at 600C to 70C, monitor the reaction by HPLC, and the conversion rate reaches more than 99% after 8 hours. The reaction was stopped, poured into 100 g of ice water for hydrolysis, allowed to stand for stratification, and the organic layer was directly transferred to the next reaction.

[0043] The third step: nitrification reaction

[0044] Put the organic layer of the second step into the reaction bottle, ...

Embodiment 3

[0048] The first step: ethyl esterification reaction

[0049] Put 0.1 mol of p-tert-butylphenol, 0.15 mol of acetyl chloride and 50ml of chloroform into the reaction bottle, reflux at 60-70°C for 4 hours, and the reaction conversion rate is 99.4% monitored by HPLC. Without treatment, it was directly transferred to the second step reaction.

[0050] Step 2: Fries rearrangement reaction

[0051] Add 0.12 moles of zinc chloride to the reaction liquid in the first step, continue to reflux, control the temperature at 60-70 degrees, monitor the reaction by HPLC, and the conversion rate reaches more than 99% after 7 hours. The reaction was stopped, poured into 100 g of ice water for hydrolysis, allowed to stand for stratification, and the organic layer was directly transferred to the next reaction.

[0052] The third step: nitrification reaction

[0053]Put the organic layer of the second step into the reaction bottle, lower the temperature to 15 degrees, then drop 17.3 g (0.11 mo...

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Abstract

The invention provides a synthesis method of 2-hydroxyl-3-nitroacetophenone. Starting from p-tert-butylphenol, the synthesis method is used for synthesizing the 2-hydroxyl-3-nitroacetophenone through four-step reaction including the steps of esterification, Fries rearrangement, nitrification and disproportionation in sequence. Compared with the prior art, the synthesis method has the advantages that raw materials are easy to obtain and the cost is low; a product obtained by disproportionation reaction mainly comprises the p-tert-butylphenol and can be recycled, so that a few of wastes are generated and the synthesis method is clean and environment-friendly; after the reaction is finished, the product can be recycled after being simply filtered, so that the cost is reduced and the emission of the wastes is reduced; and the target product can be obtained in a high yield, and the total yield reaches 70% to 80%.

Description

technical field [0001] The invention relates to a method for preparing an organic intermediate, in particular to a method for synthesizing 2-hydroxy-3-nitroacetophenone. Background technique [0002] 2-Hydroxy-3-nitroacetophenone is an organic intermediate that can be used in the synthesis of the asthma drug Pranlukast. [0003] There are not many synthetic methods of 2-hydroxyl-3-nitroacetophenone according to literature records, and it is easy for professionals to think of using 2-hydroxylacetophenone to obtain 2-hydroxyl-3-nitroacetophenone and 2-nitroacetophenone through nitration. Hydroxy-5-nitroacetophenone mixture, and then separated to obtain 2-hydroxy-3-nitroacetophenone, but the separation of the mixture is not only time-consuming and cumbersome when made according to the above method, the yield is low, and the cost is also high . The even more unsatisfactory by-product 2-hydroxy-5-nitroacetophenone has no use, and has to spend manpower and material resources t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/157C07C45/54C07C49/825C07C201/08C07C205/45C07C201/12
Inventor 易章国吴俊飞习富刚廖育能
Owner 湖北相和精密化学有限公司