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Synthetic method for 2,4-dimethoxy-methylphenyl-4-propylresorcinol

A technology of propyl resorcinol and dimethoxy group is applied in the field of synthesis of 2,4-dimethoxy-tolyl-4-propyl resorcinol, achieving stable yield and short generation period Effect

Inactive Publication Date: 2018-09-14
WUHAN JASON BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, there are almost no relevant bibliographical reports on the industrial synthesis method of 2,4-dimethoxy-tolyl-4-propyl resorcinol. Based on the above situation, the present invention provides a method for synthesizing 2,4-dimethyl New method and new process of oxy-tolyl-4-propyl resorcinol product

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] (1) In a 100ml three-neck flask, put 1.94g of 2,4-dimethoxy-3-methyl-acetophenone and 19.4g of ethyl acetate solvent in sequence, and use a cryogenic cold trap to lower the temperature of the reaction system to -5 ℃, at this temperature, 19.4g of 40wt% sodium hydroxide solution was added dropwise, and after the addition was completed, the temperature was controlled at -5℃, and 3.78g of 2,4-dibenzyloxy-benzaldehyde was gradually added, about 2.0-2.5 After adding in 1 hour, react at -5°C for 24 hours, monitor the liquid phase until the reaction of the raw material 2,4-dimethoxy-3-methyl-acetophenone is completed, and separate the organic phase and the water phase Wash with ethyl acetate 5.0g×3 times, combine all organic phases, dry the organic phase at p≤-0.098Mpa, T≤40℃, add 4.0g ethyl acetate after concentrated drying to heat the product to 30-40℃ Dissolve and clear, gradually cool down to -5°C under stirring conditions, keep stirring at this temperature for 2 hours whe...

Embodiment 2

[0038](1) In a 1000ml three-neck flask, put 19.4g of 2,4-dimethoxy-3-methyl-acetophenone and 200g of ethyl acetate solvent in sequence, and use a cryogenic cold trap to lower the temperature of the reaction system to -5°C At this temperature, add 200g of 35wt% sodium hydroxide solution dropwise. After the dropwise addition, control the temperature at -5°C and gradually add 39.0g of 2,4-dibenzyloxy-benzaldehyde for about 4.0-4.5 hours After completion, react at -5°C for 24 hours, monitor the liquid phase until the reaction of the raw material 2,4-dimethoxy-3-methyl-acetophenone is completed, and separate and collect the organic phase separately, and use acetic acid for the water phase Ethyl ester 50g × wash 3 times, combine all organic phases, dry the organic phase at p≤-0.098Mpa, T≤40°C, add 40g ethyl acetate after concentrated drying, heat the product to 30-40°C to dissolve, and Under the condition of stirring, gradually lower the temperature to -5°C. When a large amount of s...

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Abstract

The invention discloses a synthetic method for 2,4-dimethoxy-methylphenyl-4-propylresorcinol, and belongs to the technical field of synthesis. The method comprises the following steps: reacting 2,4-dimethoxy-3-methyl-acetophenone, 2,4-dibanzyloxy-benzaldehyde and strong base in a mixing system of an aqueous solution and an organic solvent A, reacting at the temperature being minus 5 DEG C-10 DEG C, and extracting and purifying after reaction is finished to obtain an intermediate I; and reacting the intermediate I, amalgam zinc and hydrochloric acid under the condition of refluxing, and extracting and purifying after reaction is finished to obtain an intermediate II; and carrying out catalytic hydrogenation reaction on the intermediate II to obtain the 2,4-dimethoxy-methylphenyl-4-propylresorcinol. The purity of the product obtained by the method is greater than 98%, and the yield is stable. The synthetic method for 2,4-dimethoxy-methylphenyl-4-propylresorcinol has the advantages of short generation period, convenience in operation, easiness in industrial production and the like.

Description

technical field [0001] The invention belongs to the technical field of synthesis, and specifically discloses a synthesis method of 2,4-dimethoxy-tolyl-4-propyl resorcinol. Background technique [0002] Resorcinol derivatives are currently reported as one of the most effective whitening agents, among which phenylethylresorcinol, hexylresorcinol, butylresorcinol, 2,4-dimethoxy-toluene 4-propyl resorcinol is a safe and efficient whitening agent that has been studied more. [0003] Phenylethyl resorcinol has excellent skin whitening effect and is one of the most active tyrosinase inhibitors reported. It can effectively even out skin tone, whiten skin tone and lighten dark spots. The freckle removal effect is 22 times that of kojic acid; it can effectively inhibit the activity of melanin synthesis by B16v melanoma cells, which is 210 times that of kojic acid and 32 times that of arbutin. Reduces skin color changes caused by UV exposure; at the same time it is an excellent anti...

Claims

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Application Information

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IPC IPC(8): C07C41/26C07C43/23
CPCC07C41/20C07C41/26C07C45/45C07C43/23C07C43/2055C07C49/84
Inventor 杨博李健雄张进军
Owner WUHAN JASON BIOTECH CO LTD
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