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Synthetic method for increasing yield of 5-chloro-1-indanone

A synthesis method and technology of indanone are applied in the synthesis field of improving the yield of 5-chloro-1-indanone, can solve the problems of many side reactions, poor selectivity, low yield and the like, and achieve improved selectivity, improved viscosity, The effect of reducing side reactions

Active Publication Date: 2020-07-28
山东京博生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0017] Aiming at the technical problems such as poor selectivity of Friedel-Crafts alkylation reaction in the prior art, many side reactions, and low yield, the present invention provides a synthetic method for improving the yield of 5-chloro-1-indanone to solve the above problems

Method used

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  • Synthetic method for increasing yield of 5-chloro-1-indanone
  • Synthetic method for increasing yield of 5-chloro-1-indanone
  • Synthetic method for increasing yield of 5-chloro-1-indanone

Examples

Experimental program
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Effect test

Embodiment 1

[0049] A kind of synthetic method of 5-chloro-1-indanone, the concrete steps are as follows:

[0050] (1) take by weighing 211.0g 3,4'-dichloropropiophenone, 400.5g aluminum trichloride and place in reaction flask, connect tail gas absorption device, open stirring, be slowly warming up to 100 ℃, and system presents molten state;

[0051] (2) When the system is in a molten state, weigh 21.1g of tetrabutylammonium bromide, add it to the reaction flask, continue to heat up, and heat up to 160°C for 1 hour; after reaching the target temperature, keep the temperature for 2 hours, and monitor the reaction by HPLC. When there is no 3,4'-dichloropropiophenone remaining, the reaction is stopped;

[0052] (3) Cool the reaction solution to 80°C, transfer it into 0-5°C water, and stir for 1 h;

[0053] (4) suction filtration, the filter cake is rinsed with water to filtrate pH=6~7, and suction filtration is carried out until no water droplets fall to obtain 337.2g of crude product;

[0...

Embodiment 2

[0063] A kind of synthetic method of 5-chloro-1-indanone, the concrete steps are as follows:

[0064] (1) take by weighing 211.0g 3,4'-dichloropropiophenone, 400.5g aluminum trichloride and place in reaction flask, connect tail gas absorption device, open stirring, be slowly warming up to 100 ℃, and system presents molten state;

[0065] (2) When the system is in a molten state, weigh 1.06g of tetrabutylammonium bromide, add it to the reaction flask, continue to heat up, and heat up to 160°C for 1 hour; after reaching the target temperature, the reaction is incubated for 4.5 hours, and the reaction is monitored by HPLC. At this time, there is no 3,4'-dichloropropiophenone remaining, and the reaction is stopped;

[0066] (3) Cool the reaction solution to 80°C, transfer it into 0-5°C water, and stir for 1 h;

[0067] (4) suction filtration, the filter cake is rinsed with water to filtrate pH=6~7, and suction filtration is carried out until no water droplets fall to obtain 311.8...

Embodiment 3

[0073] A kind of synthetic method of 5-chloro-1-indanone, the concrete steps are as follows:

[0074] (1) take by weighing 211.0g 3,4'-dichloropropiophenone, 400.5g aluminum trichloride and place in reaction flask, connect tail gas absorption device, open stirring, be slowly warming up to 100 ℃, and system presents molten state;

[0075] (2) When the system is in a molten state, weigh 21.1 g of tetrabutylammonium chloride, add it to the reaction flask, continue to heat up, and heat up to 160 ° C for 1 hour; after reaching the target temperature, the reaction is kept for 4 hours, and the reaction is monitored by HPLC. When there is no 3,4'-dichloropropiophenone remaining, the reaction is stopped;

[0076] (3) Cool the reaction solution to 80°C, transfer it into 0-5°C water, and stir for 1 h;

[0077] (4) suction filtration, the filter cake is rinsed with water to the pH of the filtrate=6~7, and the suction filtration is carried out until no water droplets fall to obtain 317.6g...

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Abstract

The invention provides a synthetic method for increasing the yield of 5-chloro-1-indanone, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: taking 3,4'-dichloropropiophenone as a raw material, adding an aprotic acid catalyst, then heating to a molten state, and then adding a phase transfer catalyst to carry out reactions; wherein the aprotic acid catalyst is one of AlCl3, ZnCl2, InCl3, TiCl4, BF3, Fe(CF3SO3)3, Fe(CF3SO3)2 and gamma-aluminum oxide; the phase transfer catalyst is one of tetrabutyl ammonium bromide, tetrabutyl ammoniumchloride, trioctyl methyl ammonium chloride, benzyl triethyl ammonium chloride, dodecyl trimethyl ammonium chloride, 18-crown-6, 15-crown-5, polyethylene glycol 400, polyethylene glycol 600 and polyethylene glycol 800. By adding the phase transfer catalyst, the selectivity of a Friedel-Crafts reaction is obviously improved, the side reaction is reduced, and the reaction yield is improved.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method for improving the yield of 5-chloro-1-indanone. Background technique [0002] 5-Chloro-1-indanone is an important organic chemical intermediate, which is widely used in the synthesis of pesticides, medicines and other chemicals. New pesticides such as Indoxacard produced from 5-chloro-1-indanone have the characteristics of high efficiency and low residue. They are projects encouraged by the national industrial policy and have very broad application prospects. According to literature reports, the main synthetic routes of this compound are as follows: [0003] Route 1: m-chlorobenzaldehyde method [0004] [0005] Route 1 uses m-chlorobenzaldehyde as the main raw material and undergoes reactions such as condensation, catalytic hydrogenation, Friedel-Crafts alkylation, etc. The synthesis steps are relatively cumbersome. And palladium ch...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/61C07C49/67
CPCC07C45/61C07C2602/24C07C49/67Y02P20/584
Inventor 冯培良时明薄蕾芳周芙蓉刘建成于连友王祥传
Owner 山东京博生物科技有限公司
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