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Paranitrophenetole and preparation method thereof

A technology of nitrophenethyl ether and p-nitrochlorobenzene, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as many side reactions, poor product quality, and breakage of ether groups, and achieve The effect of reducing side reactions and reducing the amount of water used

Inactive Publication Date: 2017-07-21
常州市正锋光电新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] P-nitrophenetole is an aromatic compound. The conventional method for preparing p-nitrophenetole is: use water or ethanol as a solvent, and take p-nitrochlorobenzene, ethanol and liquid sodium hydroxide as reactants. The transfer method is produced by etherification under the action of a catalyst and above 80°C, and the catalyst used for phase transfer is not easy to decompose and recycle, which will pollute the product
p-Nitroanisole and p-nitrophenetole have great similarity in structure, but the methoxidation reaction and ethoxylation reaction of p-nitrohalobenzene are very different, and the acidity of methanol and ethanol in raw materials is different , so the former reaction is relatively easy without the generation of by-products, while the latter reaction is more difficult and accompanied by the generation of a large number of by-products
The conventional synthesis reaction of p-nitrophenethyl ether is ethoxylation reaction, which requires high-temperature alkaline conditions to proceed. However, under high-temperature alkaline conditions, the ether group will be broken and a large amount of p-nitrophenol and its dimers will be generated. At the same time, under such conditions, various side reactions such as oxidation and coupling will occur to generate a large number of other by-products, which will affect the quality of the product
And adopt water as solvent, make reaction equilibrium shift to the left, influence the yield of product
Therefore, there are problems such as many side reactions, poor product quality and low yield in the conventional method for preparing p-nitrophenetole, and it is necessary to develop a new synthetic method for p-nitrophenetole to solve such problems

Method used

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  • Paranitrophenetole and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0012] Put 150g of p-nitrochlorobenzene, 150g of dimethyl sulfoxide, and 65g of ethanol into the reactor, slowly add 39g of solid sodium hydroxide while stirring at a temperature of 50°C, and then stir the reaction, take samples and detect p-nitro The content of chlorobenzene, when the p-nitrochlorobenzene is less than 0.5%, stop the reaction, filter to remove sodium chloride, distill ethanol and water under normal pressure, then distill dimethyl sulfoxide under reduced pressure, and wash the remaining oil layer with hot water , separated the oil layer, cooled and dried to obtain 150 grams of solid product, the content of p-nitrophenetole was 99.30%, and the reaction yield was 94%.

Embodiment 2

[0014] Put 150g of p-nitrochlorobenzene, 150g of dimethyl sulfoxide, and 60g of ethanol into the reactor, slowly add 39g of solid sodium hydroxide while stirring at a temperature of 50°C, and then stir the reaction, take samples and detect p-nitro The content of chlorobenzene, when the p-nitrochlorobenzene is less than 0.5%, stop the reaction, filter to remove sodium chloride, distill ethanol and water under normal pressure, then distill dimethyl sulfoxide under reduced pressure, and wash the remaining oil layer with hot water , separated the oil layer, cooled and dried to obtain 148 grams of solid product, the content of p-nitrophenetole was 99.08%, and the reaction yield was 93%.

Embodiment 3

[0016] Put 150g of p-nitrochlorobenzene, 150g of dimethyl sulfoxide, and 70g of ethanol into the reactor, slowly add 39g of solid sodium hydroxide while stirring at a temperature of 50°C, and then stir the reaction, take samples and detect p-nitro The content of chlorobenzene, when the p-nitrochlorobenzene is less than 0.5%, stop the reaction, filter to remove sodium chloride, distill ethanol and water under normal pressure, then distill dimethyl sulfoxide under reduced pressure, and wash the remaining oil layer with hot water , separated the oil layer, cooled and dried to obtain 150 grams of solid product, the content of p-nitrophenethyl ether was 99.17%, and the reaction yield was 94%.

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Abstract

The invention belongs to the field of organic synthesis, in particular to a p-nitrophenetole and a preparation method thereof. P-nitrochlorobenzene, ethanol and solid sodium hydroxide are used as reaction substances, and dimethyl sulfoxide is used as a solvent to perform etherification reaction at a temperature of 30-80°C to prepare p-nitrophenethyl ether. The finally obtained p-nitrophenethyl ether has a content greater than 99%, and the reaction yield is 94%.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a p-nitrophenetole and a preparation method thereof. Background technique [0002] P-nitrophenetole is an aromatic compound. The conventional method for preparing p-nitrophenetole is: use water or ethanol as a solvent, and take p-nitrochlorobenzene, ethanol and liquid sodium hydroxide as reactants. The transfer method is produced by etherification under the action of a catalyst at a temperature above 80°C, and the catalyst used for phase transfer is not easy to decompose and recover, which will pollute the product. p-Nitroanisole and p-nitrophenetole have great similarity in structure, but the methoxidation reaction and ethoxylation reaction of p-nitrohalobenzene are very different, and the acidity of methanol and ethanol in raw materials is different , so the former reaction is relatively easy without the generation of by-products, while the latter reaction is more difficult an...

Claims

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Application Information

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IPC IPC(8): C07C201/12C07C205/37
CPCC07C201/12
Inventor 徐小虎
Owner 常州市正锋光电新材料有限公司
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