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Preparation method of 1-cyclopropyl-3-(2-methylthio-4-trifluoromethylphenyl)propyl-1,3-dione

A technology of trifluoromethyl phenyl and trifluoromethyl benzoic acid, applied in the field of organic synthesis, can solve problems such as high cost, unfavorable environmental protection, and many waste acids

Active Publication Date: 2019-05-31
LIER CHEM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The technical problem solved by the present invention is that the preparation method of the existing 1-cyclopropyl-3-(2-methylthio-4-trifluoromethylphenyl) propane-1,3-dione has high cost and the waste produced More acid, not conducive to environmental protection

Method used

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  • Preparation method of 1-cyclopropyl-3-(2-methylthio-4-trifluoromethylphenyl)propyl-1,3-dione
  • Preparation method of 1-cyclopropyl-3-(2-methylthio-4-trifluoromethylphenyl)propyl-1,3-dione

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preparation example Construction

[0029] Specifically, the preparation method of 1-cyclopropyl-3-(2-methylthio-4-trifluoromethylphenyl)propane-1,3-dione includes the following steps:

[0030] (1) Mix 2-nitro-4-trifluoromethylbenzoic acid with n-butanol and concentrated sulfuric acid, and react to obtain butyl 2-nitro-4-trifluoromethylbenzoate;

[0031] (2) 2-Nitro-4-trifluoromethyl butyl benzoate is reacted with sodium methyl mercaptan to obtain butyl 2-methylthio-4-trifluoromethyl benzoate;

[0032] (3) Reaction of 2-methylthio-4-butyl trifluoromethyl benzoate with cyclopropyl ketone to obtain 1-cyclopropyl-3-(2-methylthio-4-trifluoromethylphenyl) ) Propane-1,3-dione.

[0033] The reaction formula of the method of the present invention is as follows:

[0034]

[0035] The invention selects n-butanol as the esterification raw material, which can reduce the consumption of concentrated sulfuric acid. Among them, the molar ratio of 2-nitro-4-trifluoromethyl benzoic acid to n-butanol is 1:1-16; further, in order to comple...

Embodiment 1

[0053] (1) Preparation of 2-nitro-4 butyl trifluoromethyl benzoate

[0054]

[0055] A 500mL four-neck flask was first added with 200mL of toluene, then 100g of 2-nitro-4-trifluoromethylbenzoic acid (0.425mol, 1eq), 33.1g of n-butanol (0.447mol, 1.05eq) and 4.25g of concentrated sulfuric acid ( 0.0425mol, 0.1eq), then heated to an internal temperature of 117°C to make it reflux, the water separator was separated, and the reaction was kept for 5 hours. After the reaction was kept for 5 hours, HPLC detected that there was almost no remaining 2-nitro-4-trifluoromethylbenzoic acid in the reaction solution ( 1% or less), the reaction solution is the crude product of 2-nitro-4 trifluoromethyl butyl benzoate, and the HPLC purity is 99%.

[0056] (2) Preparation of 2-methylthio-4 butyl trifluoromethyl benzoate

[0057]

[0058] Take another 1L four-neck flask, add 2.74g tetrabutylammonium bromide (0.00851mol, 0.02eq) and 164g 20% ​​sodium methyl mercaptan (0.468mol, 1.1eq), heat to 60℃ and ...

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Abstract

The invention provides a preparation method of 1-cyclopropyl-3-(2-methylthio-4-trifluoromethylphenyl)propyl-1,3-dione, and belongs to the technical field of organic synthesis. The preparation method comprises following steps: (1) mixing 2-nitro-4-trifluoromethyl benzoic acid, n-butanol, and concentrated sulfuric acid to carry out reactions to obtain butyl 2-nitro-4-trifluoromethyl benzoate; (2) reacting butyl 2-nitro-4-trifluoromethyl benzoate with sodium methyl mercaptide to obtain butyl 2-methylmercapto-4-trifluoromethyl benzoate; and (3) reacting butyl 2-methylmercapto-4-trifluoromethyl benzoate with cyclopropyl methyl ketone to obtain 1-cyclopropyl-3-(2-methylthio-4-trifluoromethylphenyl)propyl-1,3-dione. The preparation method has the advantages that the using amount of concentrated sulfuric acid and n-butanol is small, the preparation time is short, the yield is high, the purity is high, the cost is low, the generated waste gas, waste solids, and waste water are little, and the preparation method can be applied to industrial production.

Description

Technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a preparation method of 1-cyclopropyl-3-(2-methylthio-4-trifluoromethylphenyl)propane-1,3-dione. Background technique [0002] 1-Cyclopropyl-3-(2-methylthio-4-trifluoromethylphenyl)propan-1,3-dione is an important organic synthesis intermediate, which can be used to produce pesticides and weeding Pesticides and other pesticides. [0003] The prior art usually adopts the following route to prepare 1-cyclopropyl-3-(2-methylthio-4-trifluoromethylphenyl)propan-1,3-dione, because the boiling point of methanol in the esterification reaction is relatively high Low, it is difficult to increase the reaction activity by further raising the temperature. Even if a large excess of methanol is used, it takes 3.5 equivalents of concentrated sulfuric acid to react for a long time to make the in-situ yield of the product reach 87%. For example, CN1972932A discloses a method for p...

Claims

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Application Information

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IPC IPC(8): C07C319/20C07C323/22
Inventor 曾伟姚中伟梁维平左翔程柯
Owner LIER CHEM CO LTD
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