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A kind of synthetic method of 1,4-dichloro-2-(chloromethyl)-5-ethoxybenzene

A technology of ethoxybenzene and a synthesis method, applied in the field of pesticide chemistry, can solve the problems of low reaction purity and yield, poor stability of benzyl alcohol, many reaction steps, etc., and achieves good product purity, readily available raw materials, and mild conditions. Effect

Active Publication Date: 2022-04-29
JIANGSU FLAG CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] But this reaction step is many, and the stability of benzyl alcohol is poor, and by-product is many, and reaction purity and yield are not high, so need to develop a kind of efficient 1,4-dichloro-2-(chloromethyl)-5 -The synthetic method of ethoxybenzene

Method used

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  • A kind of synthetic method of 1,4-dichloro-2-(chloromethyl)-5-ethoxybenzene
  • A kind of synthetic method of 1,4-dichloro-2-(chloromethyl)-5-ethoxybenzene
  • A kind of synthetic method of 1,4-dichloro-2-(chloromethyl)-5-ethoxybenzene

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Experimental program
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Embodiment 1

[0022] ①Synthesis of 1,4-dichloro-2-ethoxybenzene

[0023] Under the protection of nitrogen, 20g of solvent N,N-dimethylformamide was added to a 200ml four-necked flask, and then 4.76g (0.045mol) of sodium carbonate solid was added, stirred evenly, and then 4.89g of 2,5-dichlorophenol ( 0.03mol), the temperature was maintained at 60°C and stirred for 20min, then ethyl iodide (5.61g, 0.036mol) was added dropwise, and the dropwise addition was completed in 30min, and the temperature was controlled at 60°C for 3 hours. Add 30g of toluene and 50g of water into the system, stir and let it stand for stratification. The upper organic phase is dried with anhydrous sodium sulfate, filtered, and desolvated under reduced pressure to obtain 1,4-dichloro-2-ethoxybenzene (5.4g yellow Liquid), yield 94.0%, qualitative content 99.0%.

[0024] ②Synthesis of 1,4-dichloro-2-(chloromethyl)-5-ethoxybenzene

[0025] Under nitrogen protection, 36g of acetic acid (0.6mol) was added to a 250ml four-...

Embodiment 2

[0028] ①Synthesis of 1,4-dichloro-2-ethoxybenzene

[0029] Under the protection of nitrogen, 20g of solvent N,N-dimethylformamide was added to a 200ml four-necked flask, and then 6.36g (0.06mol) of sodium carbonate solid was added, stirred evenly, and then 4.89g of 2,5-dichlorophenol ( 0.03mol), the temperature was maintained at 60°C and stirred for 20min, then 6.01g (0.039mol) of diethyl sulfate was added, the addition was completed in 30min, and the temperature was controlled at 60°C for 3 hours. Add 30g of toluene and 50g of water into the system, stir and let it stand for stratification. The upper organic phase is dried with anhydrous sodium sulfate, filtered, and desolvated under reduced pressure to obtain 1,4-dichloro-2-ethoxybenzene (5.3g yellow Liquid), yield 91.8%, qualitative content 99.3%.

[0030] ②Synthesis of 1,4-dichloro-2-(chloromethyl)-5-ethoxybenzene

[0031] Under nitrogen protection, 60g of acetic acid (1.0mol) was added to a 500ml four-necked flask, foll...

Embodiment 3

[0034] ①Synthesis of 1,4-dichloro-2-ethoxybenzene

[0035] Under the protection of nitrogen, 20g of solvent N,N-dimethylformamide was added to a 200ml four-necked flask, and then 6.36g (0.06mol) of sodium carbonate solid was added, stirred evenly, and then 4.89g of 2,5-dichlorophenol ( 0.03mol), the temperature was maintained at 60°C and stirred for 20min, then ethyl iodide (5.61g, 0.036mol) was added dropwise, and the dropwise addition was completed in 30min, and the temperature was controlled at 60°C for 3 hours. Add 30g of toluene and 50g of water into the system, stir and let it stand for stratification. The upper organic phase is dried with anhydrous sodium sulfate, filtered, and desolvated under reduced pressure to obtain 1,4-dichloro-2-ethoxybenzene (5.41g yellow Liquid), yield 94.2%, qualitative content 99.0%.

[0036] ②Synthesis of 1,4-dichloro-2-(chloromethyl)-5-ethoxybenzene

[0037] Under nitrogen protection, add 19.1g 1,4-dichloro-2-ethoxybenzene (0.1mol), 9.0g ...

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Abstract

The present invention relates to the technical field of pesticide chemistry, in particular to a synthesis method of 1,4-dichloro-2-(chloromethyl)-5-ethoxybenzene, comprising the following steps: Under catalysis, react with ethylating reagent to obtain 1,4-dichloro-2-ethoxybenzene; 1,4-dichloro-2-ethoxybenzene undergoes chloromethylation reaction with chloromethylating reagent to generate 1 ,4‑Dichloro‑2‑(chloromethyl)‑5‑ethoxybenzene. The synthetic method of 1,4-dichloro-2-(chloromethyl)-5-ethoxybenzene provided by the present invention is simple in operation, mild in conditions, easy to obtain raw materials, good in selectivity and high in yield; the obtained product Good purity, suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to the technical field of pesticide chemistry, in particular to a synthesis method of 1,4-dichloro-2-(chloromethyl)-5-ethoxybenzene. Background technique [0002] Chloromethylation of aromatic compounds is widely used in organic synthesis, and 1,4-dichloro-2-(chloromethyl)-5-ethoxybenzene has been used as an active intermediate in medicinal chemistry , but so far, there are few literature reports on the efficient synthesis of this compound. The inventor originally used 2,5-dichlorophenol as a raw material, first hydroxymethylated, and then added sodium carbonate according to the strong acidic nature of the phenolic hydroxyl group React with an ethylating reagent, and finally perform a chlorination reaction to obtain the target compound. [0003] [0004] But this reaction step is many, and the stability of benzyl alcohol is poor, and by-product is many, and reaction purity and yield are not high, so need to develop a kind of e...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C41/22C07C43/225
CPCC07C41/22C07C41/16C07C43/225
Inventor 陈文新张烽张璞吴耀军张春波侯远昌
Owner JIANGSU FLAG CHEM IND