Unlock instant, AI-driven research and patent intelligence for your innovation.

A new process for preparing 5-chloro-2,3-dihydro-1-indanone

A preparation process, a technology of dihydrogen, applied in the field of preparation of pesticide intermediates, can solve problems such as uneven mixing, increased equipment and energy requirements, side reactions, etc., and achieve the effect of uniform stirring, easier dispersion and contact

Active Publication Date: 2022-06-21
NANKAI CANGZHOU BOHAI NEW AREA GREENING CHEM RES CO LTD
View PDF5 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Patent CN103012086B provides a method for preparing 2,3-dihydro-1-indanone. Although this method realizes the "one-pot method" preparation process of two-step reaction, there are still two deficiencies: first, the first Step Friedel-Crafts acylation reaction, the catalysts aluminum trichloride and sodium chloride are solid at the reaction temperature and the amount added is relatively large. There is no other solvent except the raw materials. It is a liquid-solid reaction. With the gradual formation of intermediates, the system will It is viscous, and it is prone to problems such as difficulty in stirring and uneven mixing
Second, because the melting temperature of aluminum trichloride and sodium chloride molten salt is relatively high, the reaction temperature in the second step needs to be controlled above 150°C. Greatly increase the requirements for equipment and energy

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A new process for preparing 5-chloro-2,3-dihydro-1-indanone
  • A new process for preparing 5-chloro-2,3-dihydro-1-indanone
  • A new process for preparing 5-chloro-2,3-dihydro-1-indanone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Under nitrogen protection, add 40g (300mmol) aluminum trichloride, 17.5g (300mmol) sodium chloride and 2.9g (21mmol) zinc chloride to a 250ml three-necked flask, heat and stir until melting, control the temperature at 80°C, and add 4.4g (39mmol) 3.8g (30mmol) 3-chloropropionyl chloride mixed solution of chlorobenzene. After the dropwise addition, the reaction was carried out at 80° C. for 2 hours. According to NMR monitoring, the 3-chloropropionyl chloride had been completely converted to produce 3-chloro-1-(4-chlorophenyl)-1-propanone. Then the temperature was raised to 130° C., and the reaction was carried out at this temperature for 3 hours. According to NMR monitoring, the intermediates were completely converted, and 5-chloro-2,3-dihydro-1-indanone was generated. Pour the product into hydrochloric acid: ice water = 15g: 450g of hydrochloric acid and ice water mixture, then add dichloromethane to extract the product, the dichloromethane layer was washed with saturate...

Embodiment 2

[0033] The difference from Example 1 is that the amount of zinc chloride is 2.0 g (15 mmol), and 3.20 g of refined product is obtained with a yield of 64.0%.

Embodiment 3

[0035] The difference from Example 1 is that the amount of zinc chloride is 4.1g (30mmol), and 3.18g of refined product is obtained with a yield of 63.7%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention belongs to the technical field of preparation of pesticide intermediates, and provides a preparation process of 5-chloro-2,3-dihydro-1-indanone. Using 3-chloropropionyl chloride and chlorobenzene as raw materials, using a mixed molten salt of aluminum trichloride, sodium chloride and zinc chloride as a catalyst, and adopting a "one-pot method" process reaction to obtain the product 5-chloro-2,3- Dihydro-1-indanone. The invention realizes the first step of liquid-liquid reaction by directly dropping 3-chloropropionyl chloride and chlorobenzene raw materials into the molten salt under lower temperature conditions, so that the raw materials and the catalyst are easier to disperse and contact, and the stirring is more uniform. The lower melting temperature of the catalyst also enables the liquid-liquid reaction to be realized at a relatively low temperature (130°C-135°C) in the second-step reaction, which is beneficial to reduce side reactions and reduce requirements for equipment and energy.

Description

technical field [0001] The invention belongs to the technical field of preparation of pesticide intermediates, and in particular relates to a preparation process of 5-chloro-2,3-dihydro-1-indanone. Background technique [0002] 5-Chloro-2,3-dihydro-1-indanone is an important intermediate of a new pesticide variety developed by DuPont of the United States in 1992. At present, the synthesis of this product mainly includes the following methods: [0003] 1. The first synthetic method: m-chlorocinnamic acid method. [0004] In this method, m-chlorocinnamic acid is used as raw material, m-chlorophenylpropionic acid is obtained by hydrogenation, m-chlorophenylpropionyl chloride is obtained by chlorination, and finally 5-chloro-2,3-dihydro-1-indanone is obtained by ring closure. The disadvantage of this method is mainly that there is selectivity during ring closure, and a certain proportion of 7-chloro-2,3-dihydro-1-indanone will be formed, resulting in impure products and separat...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/61C07C49/697C07C45/46C07C49/80B01J35/12B01J27/10B01J27/138B01J27/125B01J35/27
CPCC07C45/46C07C45/61B01J27/10B01J27/138B01J27/125C07C2602/08B01J35/27C07C49/80C07C49/697
Inventor 常卫星左晓丹柳凌艳李靖
Owner NANKAI CANGZHOU BOHAI NEW AREA GREENING CHEM RES CO LTD