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Preparation method of 3-hydroxyl-4-methoxycinnamaldehyde

A technology of methoxycinnamaldehyde and hydroxyl group, which is applied in the field of preparing 3-hydroxy-4-methoxycinnamaldehyde, can solve the problems of many reaction by-products, low preparation efficiency, low product yield and the like, and achieves product yield Improves, shortens the reaction time, increases the effect of the activity

Inactive Publication Date: 2018-01-09
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

3-Hydroxy-4-methoxycinnamaldehyde can be prepared by condensation reaction of isovanillin and acetaldehyde in the presence of alkali metal hydroxide (U.S.Patent No.:7141263B2), but the amount of alkali that needs to be added in this method is raw material 10 times the molar weight of isovanillin, the post-treatment needs to add a large amount of hydrochloric acid for neutralization, resulting in a large amount of waste water, more reaction by-products, lower product yield (53%), and required reaction time up to 46h , resulting in low production efficiency and high cost of 3-hydroxyl-4-methoxycinnamaldehyde

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Dissolve 1.008g (0.015mol) of potassium hydroxide in 100ml of aqueous methanol (volume ratio of methanol to water: 1:1), then add 15.2g (0.1mol) of isovanillin and 0.456g of polytetrahydrofuran (the number average molecular weight is 250) , stir well to make it evenly mixed. After cooling to -5°C, 35.36 g (0.225 mol) of acetaldehyde aqueous solution with a mass fraction of 28% was continuously added dropwise to the reaction system to start the reaction, and the dropping process continued for 5 hours. After the dropwise addition, the stirring reaction was continued for 2 h, and then 1.9 ml of hydrochloric acid with a mass fraction of 36% was added for neutralization to end the reaction. After suction filtration, a light yellow crystal was obtained, which was the crude product of 3-hydroxy-4-methoxycinnamaldehyde. Add the crystals into 300ml of methanol, stir for 2h, filter with suction, and wash the filter cake with 50ml of methanol. The resulting filter cake was added...

Embodiment 2

[0014] Dissolve 0.56g (0.010mol) of potassium hydroxide in 100ml of aqueous methanol (volume ratio of methanol to water: 1:1), then add 15.2g (0.1mol) of isovanillin and 0.304g of polytetrahydrofuran (the number average molecular weight is 650) , stir well to make it evenly mixed. After cooling to 0° C., 35.36 g (0.225 mol) of acetaldehyde aqueous solution with a mass fraction of 28% was continuously added dropwise to the reaction system to start the reaction, and the dropping process continued for 4 hours. After the dropwise addition, the stirring reaction was continued for 1 h, and then 1.1 ml of hydrochloric acid with a mass fraction of 36% was added for neutralization to end the reaction. After suction filtration, a light yellow crystal was obtained, which was the crude product of 3-hydroxy-4-methoxycinnamaldehyde. Add the crystals into 300ml of methanol, stir for 2h, filter with suction, and wash the filter cake with 50ml of methanol. The resulting filter cake was added...

Embodiment 3

[0016] Dissolve 0.336g (0.006mol) of potassium hydroxide in 100ml of aqueous methanol (volume ratio of methanol to water: 1:1), then add 15.2g (0.1mol) of isovanillin and 0.304g of polytetrahydrofuran (the number average molecular weight is 1000) , stir well to make it evenly mixed. After cooling to 10° C., 19.64 g (0.125 mol) of acetaldehyde aqueous solution with a mass fraction of 28% was continuously added dropwise to the reaction system to start the reaction, and the dropping process continued for 3 hours. After the dropwise addition, the stirring reaction was continued for 1 h, and then 0.65 ml of hydrochloric acid with a mass fraction of 36% was added for neutralization to end the reaction. After suction filtration, a light yellow crystal was obtained, which was the crude product of 3-hydroxy-4-methoxycinnamaldehyde. Add the crystals into 300ml of methanol, stir for 2h, filter with suction, and wash the filter cake with 50ml of methanol. The resulting filter cake was a...

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Abstract

The invention provides a preparation method of 3-hydroxyl-4-methoxycinnamaldehyde and relates to the 3-hydroxyl-4-methoxycinnamaldehyde. The 3-hydroxyl-4-methoxycinnamaldehyde is prepared by taking potassium hydroxide as a catalyst and polytetrahydrofuran as a cocatalyst and carrying out condensation reaction on isovanillin and acetaldehyde. The adopted cocatalyst polytetrahydrofuran is polyetherdiol and can be complexed with potassium ions, so that the activity of the catalyst potassium hydroxide is improved. Compared with an existing preparation method of the 3-hydroxyl-4-methoxycinnamaldehyde, the dosage of alkali is greatly reduced, so that the amount of generated wastewater is also greatly reduced, the reaction time is greatly shortened and the yield of the product is also improved.

Description

technical field [0001] The invention relates to 3-hydroxyl-4-methoxycinnamaldehyde, in particular to a method for preparing 3-hydroxyl-4-methoxycinnamaldehyde by reacting isovanillin with acetaldehyde under the action of a catalyst and a cocatalyst. Background technique [0002] 3-Hydroxy-4-methoxycinnamaldehyde is an important intermediate in organic synthesis, which can be used in the synthesis of strong sweetener N-[N-[3-(3-hydroxy-4-methoxyphenyl)propane base]-L-α-asparagine]-L-phenylalanine-1-methyl ester (trade name Advantame). 3-Hydroxy-4-methoxycinnamaldehyde can be prepared by condensation reaction of isovanillin and acetaldehyde in the presence of alkali metal hydroxide (U.S.Patent No.:7141263B2), but the amount of alkali that needs to be added in this method is raw material 10 times the molar weight of isovanillin, the post-treatment needs to add a large amount of hydrochloric acid for neutralization, resulting in a large amount of waste water, more reaction by-p...

Claims

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Application Information

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IPC IPC(8): C07C47/277C07C45/74C07C45/81
Inventor 刘怡雪黎四芳
Owner XIAMEN UNIV
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