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A kind of method of synthesizing 6-chloro-2-methoxytoluene

A technology for methoxytoluene and dichlorotoluene, which is applied in the field of synthesizing 6-chloro-2-methoxytoluene, can solve the problems of low conversion rate, long reaction time, difficult waste water treatment and the like, and achieves simple operation and harmful effects. Small, low cost effect

Active Publication Date: 2019-04-19
JIANGSU YANGNONG CHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

European patent EP0941982 adopts cuprous cyanide as a catalyst to directly prepare 6-chloro-2-methoxytoluene under the action of sodium methoxide. The catalyst produces cyanide-containing wastewater and wastewater containing heavy metal copper, which is difficult to treat

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) In a 1000ml four-neck flask, add 300g of dimethyl sulfoxide and 100g (0.62mol) of 2,6-dichlorotoluene in sequence, raise the temperature, and when the temperature reaches 120°C, add dropwise 160g of sodium methoxide methanol solution (sodium methoxide Content 28%, 0.83mol), sodium methoxide was added dropwise, and kept at 140°C for 4h.

[0027] (2) Cool down to 40°C, add 0.1g catalyst PEG-600 (polyethylene glycol 600), and pass 9.4g methyl chloride (0.19mol) gas at this temperature to react until 6-chloro-2 The mass fraction of -hydroxytoluene is less than 1%, and the reaction is then incubated for 1 hour.

[0028] (3) Cool down to room temperature, then recover DMSO under negative pressure, and obtain 96.4 g of 6-chloro-2-methoxytoluene after post-treatment, with a content of 96.1% and a yield of 95.3%.

Embodiment 2

[0030] (1) In a 1000ml four-neck flask, add 300g of dimethyl sulfoxide and 100g (0.62mol) of 2,6-dichlorotoluene in sequence, raise the temperature, and when the temperature reaches 160°C, add dropwise 200g of sodium methoxide methanol solution (sodium methoxide Content 28%, 1.04mol), sodium methoxide was added dropwise, and kept at 160°C for 8h.

[0031] (2) Cool down to 80°C, add 0.1g of catalyst PEG-600 (polyethylene glycol 600), and feed 20g of methyl chloride (0.40mol) gas at this temperature until the mass fraction of 6-chloro-2-hydroxytoluene is less than 1 %, heat preservation reaction 2h.

[0032] (3) Cool down to room temperature, then recover DMSO under negative pressure, and obtain 96.8 g of 6-chloro-2-methoxytoluene after post-treatment, with a content of 96.0% and a yield of 95.6%.

Embodiment 3

[0034] (1) In a 1000ml four-neck flask, add 300g of 1,3-dimethyl-2-imidazolidinone and 100g (0.62mol) of 2,6-dichlorotoluene in sequence, raise the temperature, and when the temperature reaches 160°C, add dropwise 185g sodium methoxide methanol solution (sodium methoxide content 28%, 0.96mol), sodium methoxide was added dropwise, and kept at 160°C for 4h.

[0035] (2) Cool down to 40°C, add 0.1g benzyltriethylammonium chloride, feed 10g methyl chloride (0.2mol) gas at this temperature until the mass fraction of 6-chloro-2-hydroxytoluene is less than 1%, and then Insulation reaction 0.1h.

[0036] (3) Cool down to room temperature, then recover 1,3-dimethyl-2-imidazolidinone under negative pressure, and the precipitation is completed. After post-treatment, 94.0 g of 6-chloro-2-methoxytoluene is obtained, with a content of 96.5%. Yield 93.32%.

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Abstract

The invention discloses a method for synthesizing 6-chloro-2-methoxytoluene. The method comprises the following steps: dissolving 2,6-dichlorotoluene in an aprotic polar solvent, dripping sodium methylate for reacting, maintaining the temperature to be 40-170 DEG C after dripping completion, and performing a reaction for 2-20 hours; reducing the temperature to be 20-120 DEG C after temperature maintaining is completed; adding a phase transfer catalyst into the reaction solution, introducing a chloromethane gas for reacting until the mass fraction of 6-chloro-2-hydroxy methylbenzene in the reaction solution is less than 1%, and maintaining the temperature and performing a reaction for 0.1-2 hours; performing cooling to room temperature after the reaction; and recovering the aprotic polar solvent under negative pressure, performing after-treatment, thereby obtaining the 6-chloro-2-methoxytoluene. According to the method, the 6-chloro-2-methoxytoluene is synthesized by chloromethane, the reaction speed of the chloromethane is improved by using a small amount of catalysts in the method, and the chloromethane can serve as a methylation reagent under normal pressure; and moreover, the yield of the 6-chloro-2-methoxytoluene is greater than 93%, and the method disclosed by the invention is easy to operate, low in cost and slight in environmental hazards.

Description

technical field [0001] The invention relates to a method for synthesizing 6-chloro-2-methoxytoluene. Background technique [0002] 6-Chloro-2-methoxytoluene is an important pesticide intermediate, which is mainly used to synthesize methoxyfenozide, etc. [0003] The reaction of 2,6-dichlorotoluene and sodium methoxide is easy to produce 6-chloro-2-hydroxytoluene as a by-product, and 6-chloro-2-hydroxytoluene needs to be converted into 6-chloro-2-methoxytoluene through methylation. Commonly used methylating reagents are dimethyl sulfate, dimethyl carbonate, methyl iodide, methyl bromide, etc. Dimethyl sulfate is a highly toxic chemical, a potential carcinogen and a mutagen that causes chromosomal aberrations, and is volatile, toxic, corrosive and environmentally harmful. Dimethyl carbonate has weaker activity and harsher reaction conditions. Methyl iodide has better reactivity, but its price is higher. Methyl bromide also has good reactivity, but its price is relatively h...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C41/16C07C43/225
CPCC07C37/02C07C41/16C07C43/225C07C39/28
Inventor 周其奎姜友法朱建荣孙兵王明坤匡建波薛亚东
Owner JIANGSU YANGNONG CHEM