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Preparation method for synthesizing 5-chloro-1-indanone through one-step method

A technology of indanone and one-step method, which is applied in the field of preparation of one-step synthesis of 5-chloro-1-indanone, can solve the problems of increased pressure on environmental protection, unfriendly environment, high production cost, etc., and achieves low cost, environmental friendliness, and income high rate effect

Active Publication Date: 2021-10-22
佳尔科生物科技南通有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method uses a large amount of inorganic salt mixture as a solvent to produce a large amount of salty wastewater, especially aluminum-containing wastewater, which is difficult to treat and puts a lot of pressure on environmental protection. It is not friendly to the environment and has problems such as high production costs.
[0009] In summary, the prior art has technical problems such as complicated process, unfriendly environment, and high production cost.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 12.4g of chlorobenzene, 127ml of perfluoro-tert-butanol and 0.15g of D72 macroporous strong acidic resin into a 250ml tetrafluoro reaction bottle, slowly add 12.7g of 3-chloropropionyl chloride dropwise under nitrogen protection, and react at 0°C 10 hours. The catalyst was filtered off. Perfluoro-tert-butanol was distilled off under atmospheric pressure. Add 100ml of methylene chloride and 100ml of 5% (weight percent) HCl aqueous solution, separate the oil layer, and use 1% (weight percent) NaHCO 3 Aqueous solution washed to neutral. Dichloromethane was distilled off under atmospheric pressure. The residue was recrystallized with 50ml of isopropanol and dried under vacuum to obtain 15.1g of 5-chloro-1-indanone with a content of 98.5%, with a yield of over 90.7%. 1 H NMR (CDCl 3 , 300MHz): δ 7.79 (d, 1H), δ 7.23(s, 1H), δ 7.15(d, 1H), δ 2.86(t, 2H), δ 2.72(t, 2H); GC-MS, m / z (%): 167 (M+, 99%).

Embodiment 2

[0026] Add 14.6g of chlorobenzene, 64ml of perfluoro-tert-butanol and 0.65g of D72 macroporous strongly acidic resin into a 250ml tetrafluoro reaction bottle, and slowly add 12.7g of 3-chloropropionyl chloride dropwise under the protection of nitrogen, and react at 30°C 5 hours. The catalyst was filtered off. Perfluoro-tert-butanol was distilled off under atmospheric pressure. Add 100ml of methylene chloride and 100ml of 5% (weight percent) HCl aqueous solution, separate the oil layer, and use 1% (weight percent) NaHCO 3 Aqueous solution washed to neutral. Dichloromethane was distilled off under atmospheric pressure. The residue was recrystallized with 50ml of isopropanol and dried under vacuum to obtain 15.5g of 5-chloro-1-indanone with a content of 98.2%, with a yield of over 93.1%. 1 H NMR (CDCl 3 , 300MHz): δ 7.79 (d, 1H), δ 7.23(s, 1H), δ 7.15(d, 1H), δ 2.86(t, 2H), δ 2.72(t, 2H); GC-MS, m / z (%): 167 (M+, 99%).

Embodiment 3

[0028] Add 13.5g of chlorobenzene, 95ml of perfluoro-tert-butanol and 0.4g of D72 macroporous strong acidic resin into a 250ml tetrafluoro reaction bottle, and slowly add 12.7g of 3-chloropropionyl chloride dropwise under the protection of nitrogen, and react at 15°C 7.5 hours. The catalyst was filtered off. Perfluoro-tert-butanol was distilled off under atmospheric pressure. Add 100ml of methylene chloride and 100ml of 5% (weight percent) HCl aqueous solution, separate the oil layer, and use 1% (weight percent) NaHCO 3 Aqueous solution washed to neutral. Dichloromethane was distilled off under atmospheric pressure. The residue was recrystallized with 50ml of isopropanol and dried under vacuum to obtain 15.3g of 5-chloro-1-indanone with a content of 98.5%, with a yield of over 91.9%. 1 H NMR (CDCl 3 , 300MHz): δ 7.79 (d, 1H), δ 7.23(s, 1H), δ 7.15(d, 1H), δ 2.86(t, 2H), δ 2.72(t, 2H); GC-MS, m / z (%): 167 (M+, 99%).

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PUM

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Abstract

The invention provides a preparation method for synthesizing 5-chloro-1-indanone by a one-step method, wherein the preparation method comprises the following steps: mixing chlorobenzene, perfluoro tert-butyl alcohol and a catalyst macroporous strongly acidic resin, slowly dropwise adding 3-chloropropionyl chloride under the protection of nitrogen, reacting for a period of time at a certain temperature, filtering out a catalyst, and evaporating out the perfluoro tert-butyl alcohol at normal pressure; and adding dichloromethane and an HCl solution, separating out an oil layer, washing with a NaHCO3 aqueous solution until the oil layer is neutral, evaporating out dichloromethane at normal pressure, recrystallizing, and drying in vacuum to obtain the 5-chloro-1-indanone. The preparation method has the following technical effects: 1) 5-chloro-1-indanone is synthesized by a one-step method by adopting a reaction route of taking 3-chloropropionyl chloride and chlorobenzene as raw materials, taking perfluoro tert-butyl alcohol as a solvent and taking strong acid macroporous resin as a catalyst. The solvent and the catalyst in the method can be recycled and reused, and the method is environment-friendly, simple in process, high in yield and low in cost.

Description

technical field [0001] The invention belongs to the technical field of chemical industry and relates to a preparation method for one-step synthesis of 5-chloro-1-indanone. Background technique [0002] 5-Chloro-1-indanone is an important intermediate of the new pesticide variety indoxacarb (common name indoxacarb) of DuPont Company in the United States, and it is also an important pharmaceutical intermediate. Indoxacarb is a new type of sodium channel blocker developed by DuPont in 1992 and launched in 2001. It is also the first commercialized insecticide of this type. The agent blocks the sodium ion channel in the insect cells, disables the nerve cells, and prevents various pests of various crops through contact killing and stomach poisoning. Indoxacarb has a unique mechanism of action, and there is no cross-resistance with other insecticides. It is very safe for non-target insects, with low residues. It can be harvested 2 days after application, and can be used for integr...

Claims

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Application Information

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IPC IPC(8): C07C45/45C07C49/697
CPCC07C45/455C07C2602/08C07C49/697
Inventor 王彩霞周革
Owner 佳尔科生物科技南通有限公司
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