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Method for preparing alpha-metylene lactone

A technology of methylene lactone and production method, applied in the direction of organic chemistry and the like, can solve the problems of polluted reactor, unsuitable for large-scale production process and the like

Inactive Publication Date: 2014-10-29
CHEIL IND INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Also in the second step, an excess of paraformaldehyde is used, and paraformaldehyde has the potential to contaminate the reactor, so it is not suitable for large-scale production processes

Method used

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  • Method for preparing alpha-metylene lactone
  • Method for preparing alpha-metylene lactone
  • Method for preparing alpha-metylene lactone

Examples

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Embodiment approach

[0031] The present invention relates to a process for the production of α-methylene lactone comprising the steps of producing an enolate intermediate from the lactone and reacting the enolate intermediate with paraformaldehyde in order to obtain α-methylene in high yield The step of base lactone.

[0032] The present invention relates to a process for the production of α-methylene lactone comprising the steps of: (A) the step of producing an enolate intermediate by reacting the lactone with an alkyl formate in the presence of an alkoxide base; and (B) The enolate intermediate is reacted with paraformaldehyde. As a specific embodiment of the present invention, the α-methylene lactone of the present invention can be produced by the reaction represented by Reaction Formula 3.

[0033] [reaction formula 3]

[0034]

[0035] The present invention is specifically described below.

[0036] (A) Enolate intermediate production steps

[0037] In the present invention, the enola...

Embodiment 1

[0069] Sodium ethoxide (395 g, 5.81 mol) and 3.5 L of tetrahydrofuran (THF) as solvents were placed in a 5 L reactor, and the mixture was stirred at 115 rpm while maintaining the temperature of the reactor at 17°C. Ethyl formate (645 g, 8.72 mol) was quickly placed in the reactor, and γ-butyrolactone (500 g, 5.81 mol) was slowly added dropwise into the reactor over 1 hour and 30 minutes. When γ-butyrolactone is added dropwise to the reactor, the internal temperature of the reactor does not exceed 30°C, and, when γ-butyrolactone is added dropwise under stirring, the internal temperature of the reactor is kept at 17°C for 20 hours . After the reaction was completed, the precipitated compound was filtered using 3 μm filter paper, and washed with THF. The filtered compound was dried in a vacuum oven at 60°C, and α-formyl-γ-butyrolactone sodium salt was synthesized.

Embodiment 2

[0071] α-Formyl-γ-butyrolactone sodium salt was synthesized by the same method as in Example 1, except that the mixture was stirred at a speed of 115 rpm and a filter paper of 1 μm was used for filtration.

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Abstract

The present invention relates to a method for preparing alpha-metylene lactone comprising the steps of: (A) preparing an enolate intermediate by reacting lactone with alkyl formate under conditions in which an alcoxide base exists; and (B) reacting the enolate intermediate with paraformaldehyde. The method of the present invention can reduce processing time, can increase yield, and can minimize the contamination of a reactor.

Description

technical field [0001] The present invention relates to a production method of α-methylene lactone. More specifically, the present invention relates to a high-yield production process for α-methylene lactones, comprising the steps of producing an enolate intermediate from the lactone, and reacting the enolate intermediate with paraformaldehyde. Background technique [0002] To date, α-methylene lactones have been the subject of major synthetic research. In particular, α-methylene-γ-butyrolactone in α-methylene lactone is a γ-butyrolactone compound having an outer methylene group; has antitumor activity, antibacterial activity, antifungal activity, and others Biologically active; and is an important compound for the pharmaceutical industry. Copolymers of α-methylene-γ-butyrolactone: have excellent heat resistance and transparency, high refractive index, and excellent thermal and light stability; and are considered to be compatible with acrylic or styrene Copolymers of mono...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/33
CPCC07D307/33C07D307/58
Inventor 李元基李明烈金善大全寅植安盛熙洪尚铉
Owner CHEIL IND INC
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