Synthesis method of 5-Methoxy-1-[4-(trifluoromethyl) phenyl]-1-pentanone

A technology of trifluoromethyl benzonitrile and trifluoromethyl, applied in the direction of nitrile reduction and hydrolysis preparation, organic chemistry, etc., can solve the problem of long dropping time of 4-trifluoromethyl benzonitrile, inability to react sufficiently, and reaction time It can reduce the occurrence of side reactions, reduce environmental pollution, and the process is easy to control.

Active Publication Date: 2013-09-18
青岛和兴精细化学有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In WO062002691, the temperature in the coupling stage is ±5°C. Due to the strong exothermic reaction in this reaction stage, it takes a long time to add 4-trifluoromethylbenzonitrile. At the same time, the lower reaction temperature also makes the reaction time too long and cannot be reacted. full

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 1.1 Synthesis of 4-methoxybutylmagnesium chloride solution

[0024] In the pre-dried reaction kettle, put 150 grams of magnesium chips (6.17 moles), 2.5 kilograms of isopropyl ether, slowly evaporate 250 grams of isopropyl ether, lower the temperature to 20-30 °C under the protection of nitrogen, and add 34 grams of 1-chlorine - 4-Methoxybutane (0.277 mol). Add 1 gram of methyl iodide to initiate the reaction, add a toluene solution (450 grams of toluene) of 1-chloro-4-methoxybutane (654 grams, 5.333 moles) within 2 to 3 hours, and properly cool to keep the temperature at 60 to 80°C range. Keep warm for 1 hour after addition.

[0025] 1.2 Synthesis of 5-methoxy-1-[4-(trifluoromethyl)phenyl]-1-pentanone

[0026] 870 g of 4-trifluoromethylbenzonitrile (5.08 mol) and 1.2 kg of toluene were formulated into a solution, slowly added to the solution prepared in step 1.1, cooled properly to keep the temperature at 20-30°C. Keep warm for 2 hours after addition. filter.

[...

Embodiment 2

[0030] 2.1 Synthesis of 4-methoxybutylmagnesium chloride solution

[0031] In the pre-dried reaction kettle, put 150 grams (6.17 moles) of magnesium chips, 2.3 kilograms of 2-methyltetrahydrofuran, slowly evaporate 230 grams of 2-methyltetrahydrofuran, lower the temperature to 20-30 ° C under the protection of nitrogen, and add 34 gram of 1-chloro-4-methoxybutane (0.277 mol). Add 1 gram of methyl iodide to initiate the reaction, add a toluene solution (450 grams of toluene) of 1-chloro-4-methoxybutane (654 grams, 5.333 moles) within 2 to 3 hours, and properly cool to keep the temperature at 60 to 80°C range. Keep warm for 1 hour after addition.

[0032] 2.2 Synthesis of 5-methoxy-1-[4-(trifluoromethyl)phenyl]-1-pentanone

[0033] Make a solution of 870 grams of 4-trifluoromethylbenzonitrile (5.08 moles) and 1 kilogram of 2-methyltetrahydrofuran, slowly add it to the solution prepared in step 2.2, and cool it properly to keep the temperature in the range of 60-80 °C . Keep...

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Abstract

The invention discloses a synthesis method of 5-Methoxy-1-[4-(trifluoromethyl) phenyl]-1-pentanone. Firstly, parts of solvent are steamed out after magnesium chips and solvent are put in according to proportioning; then, 1-chloro-4-methoxy butane is added to react for synthesizing 4-methoxyl butyl magnesium chloride; 4-trifluoromethyl benzonitrile according to proportioning is added into the 4-methoxyl butyl magnesium chloride solution obtained in the last step to react; after reaction ends, solid products are obtained after filtering, PH value adjustment, organic phase washing by water, and solvent steaming out; then the obtained solid products after solvent is steamed out are decompressed and rectified to obtain the finished product of 5-Methoxy-1-[4-(trifluoromethyl) phenyl]-1-pentanone; the raw materials are as follows according to proportioning: 1.2-1.3 of magnesium chip, 1.1-1.2 of 1-chloro-4-methoxy butane and 1 of 4-trifluoromethyl benzonitrile. The method can obviously lower the consumption amount of the raw material, and the yield can be improved to above 80%.

Description

technical field [0001] The present invention relates to a preparation method of aryl benzophenone compounds, especially a synthesis method of 5-methoxy-1-[4-(trifluoromethyl)phenyl]-1-pentanone, which belongs to chemical technology field. Background technique [0002] The preparation methods of aryl benzophenones have been widely reported. Usually, halogenated hydrocarbons and magnesium are used to generate Grignard reagents, which are then reacted with aryl nitriles or aryl acid halides, and the products are obtained after hydrolysis. WO09958485 and WO061002691, CN200710103632, CN101134721 and other patents relate to the preparation method of 5-methoxy-1-[4-(trifluoromethyl)phenyl]-1-pentanone compound. CN200710103632 and CN101134721 use aryl carboxylic acid as the starting material, undergo acid halide with thionyl chloride, and then couple with Grignard reagent in the presence of catalyst. Patent WO09958485 introduces the use of haloalkane (preferably bromine) and magne...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/84C07C45/44
Inventor 佘蕾肖宁波隋洪珍
Owner 青岛和兴精细化学有限公司
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