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

A method for preparing 4,10-dioxatricyclo[5.2.1.0(2,6)]dec-8-en-3-one

A dioxane, 10- technology, applied in the direction of organic chemistry, can solve the problems of excessive reduction of impurities, difficult to control, affecting the performance of downstream polymerization products, etc., to achieve the effect of good reproducibility and easy operation

Active Publication Date: 2021-03-16
DALIAN JOIN KING FINE CHEM CO LTD
View PDF5 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] This route is difficult to control in the second reduction stage, and it is easy to generate excessive reduction impurities, and olefins are easy to polymerize, resulting in poor product quality and seriously affecting the performance of downstream polymerization products.

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 method for preparing 4,10-dioxatricyclo[5.2.1.0(2,6)]dec-8-en-3-one
  • A method for preparing 4,10-dioxatricyclo[5.2.1.0(2,6)]dec-8-en-3-one
  • A method for preparing 4,10-dioxatricyclo[5.2.1.0(2,6)]dec-8-en-3-one

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] The first step, into a 1L reaction flask, add potassium borohydride (53.9g, 1.0mol), 18-crown-6 (5.3g, 0.02mol) and 200.0g of tetrahydrofuran, cool to 0°C, dropwise add maleic anhydride (98.1g, 1.0mol) and 500g of tetrahydrofuran, the temperature was controlled not to exceed 25°C, it took 1h to finish dropping, and the temperature was kept stirring for 2h.

[0020] The temperature was controlled not to exceed 25° C., and 10% hydrochloric acid (500 g) was added dropwise to quench the reaction, which took 1.5 hours to finish dropping, and the stirring was continued for 0.5 hours. Extraction with ethyl acetate 300g×3, the obtained oil layers were combined and washed with water 300g×3. After washing, an ethyl acetate solution of intermediate 2 (HPLC purity 98%) is obtained. After collecting 200-300 g of ethyl acetate under negative pressure not higher than 35°C, the remaining solution is directly used in the next step.

[0021] In the second step, the ethyl acetate solutio...

Embodiment 2

[0030] first step:

[0031] Referring to the operation of the first step in Example 1, the reaction conditions were changed to obtain the results in Table 1.

[0032] Table 1

[0033]

[0034] Step 2:

[0035] Referring to the operation of the second step in Example 1, the reaction conditions were changed to obtain the results in Table 2.

[0036] Table 2

[0037]

[0038]

Embodiment 3

[0040] The first step, in the 50L reaction flask, add potassium borohydride (1.08Kg, 20.0mol), 18-crown-6 (106g, 0.4mol) and tetrahydrofuran 4.00Kg, cool to 0 ° C, dropwise add maleic anhydride ( 1.96Kg, 20.0mol) and 10.0Kg of tetrahydrofuran, the temperature was controlled not to exceed 25°C, it took 2h to finish dropping, and the stirring was continued for 3h.

[0041] The temperature was controlled not to exceed 25°C, and 10% hydrochloric acid (10.0Kg) was added dropwise to quench the reaction, which took 1.5h to finish dropping, and the stirring was continued for 0.5h. Extraction with ethyl acetate 6.00Kg×3, the obtained oil layers were combined and washed with water 6.00Kg×3. After washing, an ethyl acetate solution of intermediate 2 (HPLC purity 97%) is obtained. After 4-6 Kg of ethyl acetate is harvested under negative pressure not higher than 35° C., the remaining solution is directly used in the next step.

[0042] In the second step, the ethyl acetate solution of th...

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 discloses a method for preparing 4, 10-dioxabicyclo[5.2. 1.0(2, 6)]decane-8-ene-3-ketone, and belongs to the technical field of organic chemistry. Maleic anhydride is used as a raw material, and is sequentially subjected to a selective reduction reaction and a Diels-Alder reaction to obtain the 4, 10-dioxabicyclo[5.2. 1.0(2, 6)]decane-8-ene-3-ketone. According to the method, the rawmaterials are easy to obtain, the reaction conditions of each step are simple, the side reaction of polymerization of double bonds in the product can be effectively inhibited, verification is carriedout in kilogram-scale reaction or above, and the process batch reproducibility is good.

Description

Technical field: [0001] The invention belongs to the field of organic chemistry, in particular to a method for preparing 4,10-dioxatricyclo[5.2.1.0(2,6)]dec-8-en-3-one. Background technique: [0002] Lactone compounds are widely used in medicine, pesticides, special functional chemicals and other fields, especially lactone compounds containing olefin functional groups can be used to prepare polymeric carboxylic acid polymers. The anticorrosion agent prepared with this kind of compound has the advantages of high sensitivity, high resolution and good etching resistance, so it is widely used in fine chemical industry. [0003] 4,10-dioxatricyclo[5.2.1.0(2,6)]dec-8-en-3-one is a representative compound, and the synthetic methods reported in the existing literature are based on furan and maleic acid. The acid anhydride is used as the raw material, the Diels-Alder reaction is carried out first, and then the target product is obtained by selective reduction with sodium borohydride...

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): C07D493/18
CPCC07D493/18
Inventor 戴耀王旭艳段忠利寇美玲刘玲玲王荣良
Owner DALIAN JOIN KING FINE CHEM CO LTD