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Method for preparing high allyl alcohol ester

A technology of high allyl alcohol ester and allyl group, applied in the field of high allyl alcohol ester, can solve problems such as long reaction time, achieve the effects of simple method, reduced production cost and good industrial application prospect

Inactive Publication Date: 2009-09-02
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 2000, Yadav et al. reported that tetrahydrofuran / water was used as a solvent, and metal indium promoted the allylation reaction of geminal diacid ester and allyl bromide to generate the corresponding homoallyl alcohol ester. Although the yield of this method is better, But the reaction time is still long (Tetrahedron Letters, 2000, 41, 2695)
[0005] However, the use of metal indium for the preparation of homoallyl alcohol esters in a three-component one-pot method has not been reported in the literature.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment 1 A kind of preparation method of homoallyl alcohol ester, comprises the following steps:

[0022] (1) Put metal indium, propionaldehyde, allyl bromide, and acetyl chloride into the reaction solvent tetrahydrofuran in turn, and react at 25°C. The whole reaction process is tracked by thin-layer chromatography, that is, sampling every 5 minutes, Use a capillary tube to drip the reaction liquid spotting and the raw material propionaldehyde spotting respectively on the silica gel plate. The two spots are on the same straight line. In the exhibition bottle of the mixture of ethyl ester. After the plate transfer is completed, put the silica gel plate under an ultraviolet lamp or an iodine bottle for observation. If there is no point flush with the raw material solution propionaldehyde in the reaction solution, it indicates that the reaction is complete, and the reaction solution is obtained at this time.

[0023] The molar ratio of metal indium to propionaldehyde ...

Embodiment 2

[0027] Embodiment 2 A kind of preparation method of homoallyl alcohol ester is the same as embodiment 1.

[0028] The aldehyde compound is benzaldehyde, the allyl halide is allyl bromide, the acid chloride is propionyl chloride, and the reaction solvent is tetrahydropyran.

[0029] The molar ratio of metal indium to benzaldehyde is 1:1.0, the molar ratio of metal indium to allyl bromide is 1:1.8, the molar ratio of metal indium to propionyl chloride is 1:1.2, the molar ratio of metal indium to tetrahydropyran The ratio is 1:15.

[0030] The reaction temperature is 20°C, the reaction time is 0.6h, and the yield is 91.7%.

Embodiment 3

[0031] Embodiment 3 A kind of preparation method of homoallyl alcohol ester is the same as embodiment 1.

[0032] Wherein the aldehyde compound is p-chlorobenzaldehyde, the allyl halide is allyl chloride, the acyl chloride is n-butyryl chloride, and the reaction solvent is ether.

[0033] The molar ratio of metal indium to p-chlorobenzaldehyde is 1:0.8, the molar ratio of metal indium to allyl chloride is 1:2.0, the molar ratio of metal indium to n-butyryl chloride is 1:1.5, the molar ratio of metal indium to ether The ratio is 1:20.

[0034] The reaction temperature is 15°C, the reaction time is 0.8h, and the yield is 93.5%.

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PUM

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Abstract

The invention relates to a method for preparing high allyl alcohol ester. In the method, metal indium is used as an accelerant, and an aldehyde compound, an allyl halide and an acylating agent are mixed at one time to react at a temperature of between 5 and 30 DEG C to form the high allyl alcohol ester. The method adopts a three-composition one-pot serial reaction requiring mild conditions and short time, is simple in post treatment and high in yield, can realize large-scale production and has a good industrial application prospect.

Description

technical field [0001] The invention relates to homoallyl alcohol esters in the field of organic synthetic chemistry, in particular to a preparation method of homoallyl alcohol esters. Background technique [0002] Homoallyl alcohol esters, as a class of important organic synthesis intermediates, not only have important uses in the synthesis of medicine and natural products, but also in the preparation of allyl ester prepolymers, allyl ester monomer modification and other Unsaturated polyester resins have also been widely used. [0003] In 1998, Mohan et al. reported that Bi(OTf) 3 (Bismuth trifluoromethanesulfonate) or Sc(OTf) 3 (Scandium trifluoromethanesulfonate) is a catalyzer, reacts in acetonitrile with aldehyde, acetic anhydride, allyltrimethylsilane, thereby obtains corresponding homoallyl alcohol acetate, but this method yield is lower, and reaction The time is longer, and the catalyst is more expensive (Synthesis (Synthesis), 1998, 1823). In 1999, Chandrasekhar...

Claims

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Application Information

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IPC IPC(8): C07C67/14C07C67/08C07C69/145C07C69/157C07C69/24C07C69/36C07C69/78C07C69/767C07C69/614C07C303/28C07C309/73C07C309/75C07C253/30C07C255/55
Inventor 杜正银李艳春王芬周万伟
Owner NORTHWEST NORMAL UNIVERSITY
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