Novel method for synthesizing 3-oxacyclobutanol

A technology for oxetanol and epichlorohydrin, which is applied in the field of synthesizing 3-oxetanol, can solve the problems of high price of 3-oxetanol, hinder application and development, etc. Environmentally friendly and easy-to-use effects

Pending Publication Date: 2019-02-05
柳州丰康泰科技有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the price of 3-oxetanol is extremely expensive, which seriously hinders its further application and development in organic chemistry and biomedicine

Method used

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  • Novel method for synthesizing 3-oxacyclobutanol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) Add 139g of epichlorohydrin and 90g of glacial acetic acid into a 500mL reaction bottle, then add 0.6g of ferric chloride, raise the temperature to 70°C, and stir for 7 hours.

[0027] (2) Add 1.0g of p-toluenesulfonic acid to the reaction solution, slowly add 80g of vinyl ethyl ether dropwise, and control the dropping temperature at 40°C. After the dropwise addition, continue to stir and react at 40°C for 2 hours, then cool down to 0 0.9 g of p-toluenesulfonic acid was added, and the reaction was stirred at 40° C. for 4 hours to obtain a reaction solution.

[0028] (3) Add 345g of 50% NaOH solution into another 1000mL reaction bottle, raise the temperature to 110°C, slowly add the reaction liquid obtained in step (2) dropwise, and control the temperature during the dropping process at 110°C. Stir the reaction at 110°C for 7 hours, lower the temperature to 20°C, add 145g of water, 383g of dichloromethane, and 190g of saturated saline into the reaction bottle, stir a...

Embodiment 2

[0031] (1) Add 13.9kg of epichlorohydrin and 9kg of glacial acetic acid into a 50L reactor, and then add 60g of ferric chloride. The temperature was raised to 70°C, and the reaction was stirred for 7 hours.

[0032] (2) Add 100g of p-toluenesulfonic acid to the reaction solution, slowly add 8kg of vinyl ethyl ether dropwise, and control the dropping temperature at 40°C. After the dropwise addition, continue to stir and react at 40°C for 2 hours, then cool down to 0°C , continue to add 90g of p-toluenesulfonic acid, and continue to stir and react at 40°C for 4 hours to obtain a reaction solution.

[0033] (3) Add 34.5kg of 50% NaOH solution into another 100L reaction bottle, raise the temperature to 110°C, slowly add the reaction solution in step (2), and control the temperature during the dropping process at 110°C. Stir and react at 110°C for 7 hours, cool down to 20°C, add 14.5kg of water, 38.3kg of dichloromethane, and 19kg of saturated saline into the reaction bottle, stir...

Embodiment 3

[0036] (1) Add 139g of epichlorohydrin and 90g of glacial acetic acid into a 500mL reaction bottle, then add 1.1g of ferric bromide, raise the temperature to 70°C, and stir for 7 hours.

[0037] (2) Add 1.2g of 2-naphthalenesulfonic acid to the reaction solution, slowly add 80g of vinyl ethyl ether dropwise, and control the dropping temperature at 40°C. After the dropwise addition, continue to stir and react at 40°C for 2 hours, then cool down to 0°C , continue to add 1.1 g of 2-naphthalenesulfonic acid, and continue to stir and react at 40° C. for 4 hours to obtain a reaction solution.

[0038] (3) Add 483g of 50% KOH solution into another 1000mL reaction bottle, raise the temperature to 110°C, slowly add the reaction solution obtained in step (2) dropwise, and control the temperature during the dropping process at 110°C. Stir the reaction at 110°C for 7 hours, lower the temperature to 20°C, add 145g of water, 383g of dichloromethane, and 190g of saturated saline into the react...

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Abstract

The invention provides a novel method for synthesizing 3-oxacyclobutanol. The novel method is characterized in that epoxy chloropropane and glacial acetic acid are taken as raw materials, a catalyst is used for catalyzing the ring-opening reaction; under an organic strong acid condition, vinyl ethyl ether is added to perform upper protecting group reaction; under a strong-alkaline condition, ring-forming reaction is performed to obtain a key intermediate solution; the intermediate solution is extracted, concentrated and rectified to obtain an intermediate; catalysis amount of organic strong acid is used in the solvent by the intermediate to perform deprotection to obtain a 3-oxacyclobutanol crude product; the crude product is neutralized to be meta-alkalescent with weak alkaline, and is concentrated and rectified to obtain the 3-oxacyclobutanol product. The novel method has the characteristics of being cheap in raw materials, short in route, free of dangerous reagent, avoiding use of dangerous chemicals such as diazomethane, butyl lithium or 1,3-dichloroacetone, so that the synthesis method for 3-oxacyclobutanol can be safely amplified, and therefore, large-scale production can beperformed; and moreover, the 3-oxacyclobutanol is low in price, and is convenient to popularize.

Description

technical field [0001] The invention relates to a new method for synthesizing 3-oxetanol. Background technique [0002] In the research and development of small drug molecules, because certain positions of small drug molecules are easily biodegraded and lead to loss of activity, a disubstituted methyl group is usually introduced at these positions to avoid biodegradation of active small drug molecules. However, the introduction of a disubstituted methyl group will greatly increase the lipophilicity of the active drug molecule, which may make the small drug molecule more easily metabolized. Therefore, finding a more stable small group that does not change its lipophilicity to replace the disubstituted methyl group has become a very important and urgent goal in the development of small drug molecules. Eric Carreira et al found that the introduction of 3-oxetane on the small drug molecule can reduce its lipophilicity, increase its solubility, prevent the molecule from being de...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D305/08
CPCC07D305/08Y02P20/55
Inventor 杨琛陆承棣欧韦福欧阳葭
Owner 柳州丰康泰科技有限公司
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