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Preparation method of octyl (R)-2-(4-chloro-2-methylphenoxy) propionate root retarder

A technology of ethyl toluenesulfonylpropionate and methylphenoxy, which is applied in the field of preparation of octyl-2-propionate root inhibitor, and achieves the effects of high yield, mild reaction conditions and simple process operation

Active Publication Date: 2017-12-15
KESHUN WATERPROOF TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The general synthesis method of phenoxycarboxylate compounds is to carry out by the direct esterification of phenoxycarboxylic acid and alcohol, but for some higher aliphatic long-chain alcohols, it is more difficult to pass direct esterification because of the effects of activity, steric hindrance, etc. The yield of the final target product

Method used

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  • Preparation method of octyl (R)-2-(4-chloro-2-methylphenoxy) propionate root retarder
  • Preparation method of octyl (R)-2-(4-chloro-2-methylphenoxy) propionate root retarder
  • Preparation method of octyl (R)-2-(4-chloro-2-methylphenoxy) propionate root retarder

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Embodiment 1

[0029] A preparation method of (R)-2-(4-chloro-2-methylphenoxy) octyl propionate root inhibitor, comprising the following preparation steps:

[0030] The synthesis of S1.(S)-2-ethyl p-toluenesulfonyl propionate, concrete steps are as follows:

[0031] Add 118.0 g (1.0 mol) of L-ethyl lactate, 191.0 g (1.0 mol) of p-toluenesulfonyl chloride and 700 mL of toluene into a 2L three-neck round bottom flask equipped with a mechanical stirring device, stir at room temperature to dissolve all the solids and mix well , began to add 168.0 mL (1.2 mol) of triethylamine dropwise, and the drop was completed within 1 h. Continue the mechanical stirring reaction at 28°C to 35°C, monitor the reaction process by TLC, add water to the reaction system and continue stirring for half an hour after the raw materials have reacted, separate the liquid with a separatory funnel, and backwash the water phase twice with dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfat...

Embodiment 2

[0037] The difference between this embodiment and Example 1 is that the specific steps for the synthesis of S1. (S)-2-ethyl p-toluenesulfonylpropionate are: add L- 29.5g (0.25mol) of ethyl lactate, 47.8g (0.25mol) of p-toluenesulfonyl chloride and 175mL of toluene were stirred at room temperature to dissolve all the solids and mix evenly. Start to add 0.275mol of pyridine dropwise and finish the dropwise within 0.5h. Continue the mechanical stirring reaction at 28°C to 35°C, monitor the reaction process by TLC, add water to the reaction system and continue stirring for half an hour after the raw materials have reacted, separate the liquid with a separatory funnel, and backwash the water phase twice with dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated, and 60.6 g of light yellow transparent oily product (S)-2-ethyl p-toluenesulfonylpropionate was obtained after vacuum filtration. Others are the...

Embodiment 3

[0039] The difference between this embodiment and Example 1 is that the specific steps for the synthesis of S1. (S)-2-ethyl p-toluenesulfonylpropionate are: add L- Ethyl lactate 29.5g (0.25mol), p-toluenesulfonyl chloride 47.8g (0.25mol) and 175mL toluene, stir at room temperature to dissolve all the solids and mix evenly, start to drop 0.275mol of 4-dimethylaminopyridine, within 0.5h Drip finished. Continue the mechanical stirring reaction at 28°C to 35°C, monitor the reaction process by TLC, add water to the reaction system and continue stirring for half an hour after the raw materials have reacted, separate the liquid with a separatory funnel, and backwash the water phase twice with dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated, and 62.0 g of light yellow transparent oily product (S)-2-ethyl p-toluenesulfonylpropionate was obtained after vacuum filtration. Others are the same as embodime...

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Abstract

The invention discloses a preparation method of octyl (R)-2-(4-chloro-2-methylphenoxy) propionate which can be used as a root retarder. The preparation method comprises the following steps: with ethyl L-lactate as a raw material, sulfonating together with p-toluenesulfonyl chloride to obtain a corresponding sulfonyl ester compound; etherifying the sulfonyl ester compound and 4-chloro-o-cresol to obtain a corresponding aromatic ether ester compound; and finally, performing transesterification on the ether ester compound and n-octyl alcohol to obtain octyl (R)-2-(4-chloro-2-methylphenoxy) propionate. Octyl (R)-2-(4-chloro-2-methylphenoxy) propionate prepared by the preparation method provided by the invention is high in optical content, relatively small in optical loss of raw materials and relatively high in yield. The invention establishes a reaction system with the characteristics of simple preparation process, mild reaction condition and low cost, so that the problems that the compound is imported and has a scarce source are solved to a certain extent.

Description

technical field [0001] The invention relates to the field of organic synthesis, more specifically, to a preparation method of (R)-2-(4-chloro-2-methylphenoxy)propionate octyl inhibitor. Background technique [0002] In 1934, Kogl Fritz et al. found that phenoxycarboxylic acid compounds were a class of plant growth regulators similar to indole acetic acid. This class of plant growth regulators had a good herbicidal effect at high doses and was a good class of plant growth regulators. chemical herbicides. This type of herbicide has the advantages of low price, fast weeding speed, wide weeding spectrum, and no residue, etc., and occupies an important position in the entire chemical weeding. 2,4-D, 2-methyl-4-chlorophenoxyacetic acid (MCPA) and 2,4,5-trichlorophenoxyacetic acid (2,4,5-T) have been Commercialized as a better herbicide. The herbicidal effect of 2-methyl-4-chloropropionic acid (MCPP) is similar to that of 2,4-D, which can effectively control quinoa, swine worms ...

Claims

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Application Information

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IPC IPC(8): C07C67/03C07C69/712
CPCC07C67/03C07C67/31C07C303/28C07B2200/07C07C309/73C07C69/712
Inventor 朱月泉龚兴宇
Owner KESHUN WATERPROOF TECH CO LTD
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