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Synthesis method of 2-(2, 6-diethyl-4-methyl benzene) diethyl malonate

A technology of diethyl malonate and synthesis method, which is applied to the preparation of carboxylic acid esters, chemical instruments and methods, and the preparation of organic compounds, and can solve problems such as decomposition of diazonium salts, three wastes in aqueous systems, instability, etc., and achieve Less decomposition, faster reaction speed, and the effect of making up for low temperature kinetic energy

Active Publication Date: 2019-02-15
JIANGSU FUDING CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this method, 2-(2,6-diethyl-4-methylbenzene) diethyl malonate yield is low, at 60-78%
Simultaneously, when preparing 2,6-diethyl-4-methylbromobenzene, hydrobromic acid solution is used as the reaction solvent, and sodium nitrite aqueous solution is used as the diazotization reagent, and the diazonium salt is unstable in the aqueous system. And the reaction temperature is as high as 60-90°C, which easily leads to the decomposition of diazonium salt, resulting in too many by-products. The reaction solution needs to be extracted, concentrated, and vacuum distilled to obtain relatively pure 2,6-diethyl-4-methyl bromide Benzene enters the next reaction; in addition, the aqueous system will also cause three wastes, which is not friendly to the environment

Method used

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  • Synthesis method of 2-(2, 6-diethyl-4-methyl benzene) diethyl malonate
  • Synthesis method of 2-(2, 6-diethyl-4-methyl benzene) diethyl malonate
  • Synthesis method of 2-(2, 6-diethyl-4-methyl benzene) diethyl malonate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Step (1), add 500g of acetonitrile into the four-necked flask, put in 163.3g (1mol) 2,6-diethyl-4-methylaniline, 1.6g of cuprous chloride, cool down to 5-10°C, drop 123g (1.05mol) of isoamyl nitrite, the temperature is controlled at 5-10°C during the dropwise addition, after the dropwise addition is completed, the reaction is kept for about 2 hours, and the reaction is completed, and the diazonium solution is kept for later use.

[0031] Step (2), add 176g (1.1mol) of diethyl malonate and 300g of N,N-dimethylformamide into the four-necked flask, cool down to 0-5°C, and add 136g (1.2mol) of t- Potassium butoxide, control the temperature at 0-5°C, after the feeding is completed, slowly raise the temperature to 15-20°C, react for 1 hour, add the diazonium solution prepared in step (1) dropwise to the reaction liquid on the principle of not flushing, control The temperature is 15-20°C. After the dropwise addition is completed, the reaction is kept for 1.5 hours, and the rea...

Embodiment 2

[0033] Step (1), add 500g tetrahydrofuran into the four-neck flask, put in 163.3g 2,6-diethyl-4-methylaniline, 1.6g cuprous iodide, cool down to 5-10°C, add dropwise 123g nitrous acid For isoamyl ester, control the temperature at 5-10°C. After the dropwise addition, keep the reaction for about 2 hours. After the reaction is over, keep the diazonium solution for standby.

[0034] Step (2), add 176g of diethyl malonate and 300g of N,N-dimethylformamide into the four-neck flask, cool down to 0-5°C, add 136g of potassium tert-butoxide in batches, and control the temperature from 0 to 5°C. 5°C, after the feeding is finished, slowly raise the temperature to 15-20°C, react for 1 hour, then dropwise add the diazonium solution prepared in step (1) to the reaction solution, control the temperature at 15-20°C, after the dropwise addition, keep warm for reaction After 1.5 hours, the reaction ended. The reaction solution was added to 1000 g of water, stirred for 0.5 hours, cooled to 0-5° ...

Embodiment 3

[0036] Step (1), add 500g of tetrahydrofuran into the four-neck flask, put in 163.3g of 2,6-diethyl-4-methylaniline, 2.4g of cuprous iodide, cool down to 5-10°C, add dropwise 123g of nitrous acid For isoamyl ester, control the temperature at 5-10°C. After the dropwise addition, keep the reaction for about 2 hours. After the reaction is over, keep the diazonium solution for standby.

[0037] Step (2), add 176g of diethyl malonate and 300g of N,N-dimethylformamide into the four-neck flask, cool down to 0-5°C, add 136g of potassium tert-butoxide in batches, and control the temperature from 0 to 5°C. 5°C, after the feeding is finished, slowly raise the temperature to 15-20°C, react for 1 hour, then dropwise add the diazonium solution prepared in step (1) to the reaction solution, control the temperature at 15-20°C, after the dropwise addition, keep warm for reaction After 1.5 hours, the reaction ended. The reaction solution was added to 1000 g of water, stirred for 0.5 hours, coo...

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Abstract

The invention discloses a synthesis method of 2-(2, 6-diethyl-4-methyl benzene) diethyl malonate. The synthesis method comprises the following steps: in the presence of a catalyst, performing a reaction on 2, 6-diethyl-4-methylaniline and isoamyl nitrite, so as to obtain 2, 6-diethyl-4-methyl phenyl diazonium salt; performing a reaction on the 2, 6-diethyl-4-methyl phenyl diazonium salt and diethyl malonate in an alkaline condition, so as to obtain the 2-(2, 6-diethyl-4-methyl benzene) diethyl malonate. The yield of the 2-(2, 6-diethyl-4-methyl benzene) diethyl malonate can reach about 85%, and the maximum yield of the 2-(2, 6-diethyl-4-methyl benzene) diethyl malonate can reach 92%; a non-water system is adopted, so that the possibility of generation of three wastes is greatly reduced. The isoamyl nitrite is taken as a diazotization reagent, so that in the present of the catalyst, the reaction speed is increased, and the low-temperature kinetic energy is compensated; the produced diazonium salt is relatively stable at low temperature and in the non-water system, less diazonium salt is decomposed, and the yield of a diazotization reaction is near 100%.

Description

technical field [0001] The invention belongs to the field of pesticide synthesis, in particular to a method for synthesizing diethyl 2-(2,6-diethyl-4-methylbenzene)malonate. Background technique [0002] Pinoxaden was developed by Syngenta and launched in 2006. Pinoxaden belongs to the new phenylpyrazoline herbicides and is an acetyl-CoA carboxylase (ACC) inhibitor, which causes fatty acid synthesis to be blocked, cell growth and division to stop, cell membrane lipid-containing structure to be destroyed, and weeds to die . Pinoxaden has systemic conductivity and is mainly used in grains to control gramineous weeds after emergence. The dosage of active ingredients is 30-60g / hm 2 . [0003] The structural formula of pinoxaden is as follows: Chemical name: 8-(2,6-diethyl-4-methylphenyl)-1,2,4,5-tetrahydro-7-oxo-7H-pyrazol[1,2-d][1 ,4,5] Oxadiazepine-9-yl-2,2-dimethylpropionate; CAS No.: 243973-20-8. [0004] Diethyl 2-(2,6-diethyl-4-methylbenzene)malonate is an intermedi...

Claims

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Application Information

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IPC IPC(8): C07C67/343C07C69/612
CPCC07C67/343C07C245/20C07C69/612
Inventor 常青张胜山
Owner JIANGSU FUDING CHEM
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