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Method for synthesizing 2,6-diethyl-4-methylphenylacetate

A technology of methyl phenylacetate and methyl phenylboronic acid, which is applied in the field of organic synthesis, can solve the problems of expensive catalysts, complex reaction types, and harsh equipment requirements, and is suitable for large-scale industrial production, avoiding precious metal catalysts, and simplifying the production process. The effect of craft

Pending Publication Date: 2021-07-16
JIANGSU FLAG CHEM IND
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0018] In summary, the preparation methods have problems such as high toxicity of raw materials, many synthesis steps, expensive catalysts, complex reaction types, and harsh equipment requirements.

Method used

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  • Method for synthesizing 2,6-diethyl-4-methylphenylacetate
  • Method for synthesizing 2,6-diethyl-4-methylphenylacetate

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Embodiment 1

[0035] In a 500mL dry four-necked flask, vacuumize and replace the system with nitrogen three times, then add 200mL of anhydrous tetrahydrofuran and 40g of 2,6-diethyl-4-methylbromobenzene (molecular weight 227.15, 176.1mmol , 1eq), the temperature was cooled to -65°C in a dry-ice acetone bath, and 84.5mL of n-butyl lithium in n-hexane (2.5mol / L, 211.31mmol, 1.2eq) was slowly added dropwise. After about 40 minutes of dripping, continue stirring at -65°C for 0.5h. Then slowly add 27.45g of borane trimethyl ester (molecular weight 103.91, 264.14mmol, 1.5eq) dropwise, and drop it for about 30 minutes, then continue to stir at -65°C for 0.5h, then let the dry ice acetone bath volatilize naturally to raise the temperature of the reaction solution Stir overnight at room temperature. Add 100 mL of 1 mol / L dilute hydrochloric acid to quench the reaction solution, then extract twice with 100 mL of ethyl acetate, combine the organic phases and concentrate to dryness to obtain a crude p...

Embodiment 2

[0038] In a 500mL dry four-necked flask, vacuumize and replace the system with nitrogen three times, then add 200mL of anhydrous tetrahydrofuran and 40g of 2,6-diethyl-4-methylbromobenzene (molecular weight 227.15, 176.1mmol , 1eq), the temperature was cooled to -65°C in a dry-ice acetone bath, and 74.0 mL of n-butyl lithium in n-hexane (2.5 mol / L, 184.9 mmol, 1.05 eq) was slowly added dropwise. After about 35 minutes of dripping, continue to stir at -65°C for 0.5h. Then slowly add 20.13g borane trimethyl ester (molecular weight 103.91, 193.7mmol, 1.1eq) dropwise, and the dropwise is completed in about 20 minutes. After the dropwise operation, continue to stir at -65°C for 0.5h, then let the dry ice acetone bath volatilize naturally to raise the temperature of the reaction solution. Stir overnight at room temperature. Add 100 mL of 1 mol / L dilute hydrochloric acid to quench the reaction solution, then extract twice with 100 mL of ethyl acetate, combine the organic phases and ...

Embodiment 3

[0042] In a 1000mL dry four-neck flask, vacuumize and replace the system with nitrogen three times, then add 200mL of anhydrous tetrahydrofuran and 40g of 2,6-diethyl-4-methylbromobenzene (molecular weight 227.15, 176.1mmol , 1eq), the temperature was cooled to -65°C in a dry-ice acetone bath, and 105.6mL of n-butyl lithium in n-hexane (2.5mol / L, 264.1mmol, 1.5eq) was slowly added dropwise. After about 50 minutes of dripping, continue stirring at -65°C for 0.5h. Then slowly add 36.60g of borane trimethyl ester (molecular weight 103.91, 352.2mmol, 2.0eq) dropwise, and drop it in about 45 minutes, continue stirring at -65°C for 0.5h, then let the dry ice acetone bath volatilize naturally to raise the temperature of the reaction solution Stir overnight at room temperature. Add 150 mL of 1mol / L dilute hydrochloric acid to quench the reaction solution, then extract twice with 100 mL of ethyl acetate, combine the organic phases and concentrate to dryness to obtain a crude product, ...

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Abstract

The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing 2,6-diethyl-4-methylphenylacetate by taking 2,6-diethyl-4-methylbromobenzene as a raw material, which comprises the following steps: firstly reacting 2,6-diethyl-4-methylbromobenzene with n-butyllithium and then conducting reacting with borane trimethyl ester to generate 2,6-diethyl-4-methylphenylboronic acid; and reacting the 2,6-diethyl-4-methylphenylboronic acid with glycine alkyl ester hydrochloride to generate the 2,6-diethyl-4-methylphenylacetate. The preparation method of the 2,6-diethyl-4-methyl phenylacetate provided by the invention has the advantages that the steps are fewer, the use of an expensive noble metal catalyst and a highly toxic cyaniding reagent is avoided, the cost is reduced, the process is simplified, the yield is higher, the defects in the prior art are overcome, and the preparation method is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing 2,6-diethyl-4-methylphenylacetate by using 2,6-diethyl-4-methylbromobenzene as a raw material. Background technique [0002] 2,6-Diethyl-4-methylphenylacetic acid methyl ester, 2,6-diethyl-4-methylphenylacetic acid ethyl ester or 2,6-diethyl-4-methylphenylacetic acid n-propyl Esters are important fine chemical intermediates. They are widely used in the fields of medicine and pesticides. In particular, they are the key intermediates of the herbicide pinoxaden, which belongs to the new phenylpyrazoline compounds and has a very promising market prospect. broad. [0003] About the synthetic technology of 2,6-diethyl-4-methylphenylacetate, there are mainly the following methods with reference to domestic and foreign literature: [0004] 1. The synthesis method of methyl 2,6-diethyl-4-methylphenylacetate disclosed in DE102004053191A1, the reaction ...

Claims

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Application Information

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IPC IPC(8): C07C67/343C07C69/612C07F5/02
CPCC07C67/343C07F5/025
Inventor 卜龙吴耀军张璞高鹋骆文侯远昌
Owner JIANGSU FLAG CHEM IND
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