Method for preparing xanthoxylin

A technology of Zanthoxylin and solid-liquid ratio, applied in chemical instruments and methods, preparation of carbon-based compounds, preparation of organic compounds, etc., can solve problems such as unsatisfactory yield, achieve low cost, high yield, and achieve green The effect of industrial production

Inactive Publication Date: 2011-05-25
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In this synthetic method, the yield of the acetylation part using acetonitrile and acetic acid method is not ideal; and the dimethyl sulfate used in the methylation reaction is a highly toxic substance

Method used

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  • Method for preparing xanthoxylin
  • Method for preparing xanthoxylin
  • Method for preparing xanthoxylin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] (1) Weigh 10g of phloroglucinol, add 40mL ethyl acetate according to the solid-liquid ratio of 1:4 to dissolve, then add 40mL of acetic anhydride according to the solid-liquid ratio of 1:4, stir at room temperature, and then add 40mL of three Boron fluoride ether solution; then heated to 40°C and reacted for 10 hours; 40mL of water was added to the reaction solution, stirred for 0.5h, and the solvent was distilled off under reduced pressure. The precipitated solid was weighted with water with a solid-to-liquid ratio of 1:15 After crystallization, 2,4,6-trihydroxyacetophenone is obtained; the yield is 86.25%, 1 HNMR (CDCl 3 ) Characterization: δ12.23(s, 2H), δ10.38(s, 1H), δ5.79(s, 2H), δ2.54(s, 3H);

[0030] (2) Add 5g of 2,4,6-trihydroxyacetophenone obtained in step (1) to 5g of anhydrous potassium carbonate at a mass ratio of 2,4,6-trihydroxyacetophenone to base of 1:1, Then add 40 mL of dimethyl sulfoxide according to the solid-liquid ratio of 1:4. Under stirring at roo...

Embodiment 2

[0032] (1) Weigh 10g of phloroglucinol, add 10mL of toluene according to the solid-to-liquid ratio of 1:1 to dissolve, then add 100mL of acetic acid according to the solid-to-liquid ratio of 1:10, stir at room temperature, and then add acetic acid and other substances The anhydrous aluminum trichloride; then heated to 120 ℃, reacted for 6 hours; add 100mL of water to the reaction solution, stir for 1h, vacuum distillation to remove the solvent, the precipitated solid with solid-liquid ratio of 1:5 water Recrystallize to obtain 2,4,6-trihydroxyacetophenone; the yield is 70%, 1 HNMR (CDCl 3 ) Characterization: δ12.23(s, 2H), δ10.38(s, 1H), δ5.79(s, 2H), δ2.54(s, 3H);

[0033] (2) Add 5g of 2,4,6-trihydroxyacetophenone obtained in step (1) to 25g of anhydrous sodium carbonate at a mass ratio of 2,4,6-trihydroxyacetophenone to base of 1:5, Then add 30mL dimethyl sulfoxide according to the solid-liquid ratio of 1:1. Under stirring at room temperature, add 300mL of dimethyl carbonate a...

Embodiment 3

[0035] (1) Weigh 10g of phloroglucinol, add 100mL of toluene according to the solid-liquid ratio of 1:10 to dissolve, then add 200mL of acetyl chloride according to the solid-to-liquid ratio of 1:10, stir at room temperature, and add acetyl chloride, etc. Anhydrous zinc chloride; then heated to 20°C and reacted for 8 hours; add 200 mL of water to the reaction solution, stir for 1 hour, distill under reduced pressure to remove the solvent, and use water with a solid-liquid ratio of 1:20 to precipitate the solid After recrystallization, 2,4,6-trihydroxyacetophenone is obtained; the yield is 76%, 1 HNMR (CDCl 3 ) Characterization: δ12.23(s, 2H), δ10.38(s, 1H), δ5.79(s, 2H), δ2.54(s, 3H);

[0036] (2) Add 5g of 2,4,6-trihydroxyacetophenone obtained in step (1) to 50g of anhydrous sodium carbonate at a mass ratio of 2,4,6-trihydroxyacetophenone to base of 1:10, Then add 550mL of dimethyl sulfoxide according to the solid-liquid ratio of 1:10, add 1100mL of dimethyl carbonate according ...

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Abstract

The invention provides a method for preparing xanthoxylin. The method comprises the following steps of: performing acylation and esterification reactions on phloroglucinol and an acylation reagent in the presence of lewis acid; rearranging phenolic ester to obtain 2,4,6-trihydroxy acetophenone; and performing methylation reaction on the 2,4,6-trihydroxy acetophenone and a methylation reagent under an alkaline condition to prepare the xanthoxylin. The method has a simple process, high yield and rich raw material resources, and is low in cost; a product is easy and convenient to separate and purify; the reagents are environmentally-friendly; and the environmentally-friendly industrial production of the xanthoxylin can be realized.

Description

Technical field [0001] The invention relates to a method for preparing xanthoxylin, which belongs to the field of medicine synthesis. Background technique [0002] Xanthophyllin, systematically named 2-hydroxy-4,6-dimethoxyacetophenone, and its structural formula is shown in formula I. Xanthoxylin (xanthoxylin, XT) is a compound extracted from the root bark of the Euphorbia chinensis plant. Chinese tallow tree is a traditional Chinese medicinal material. The root bark of tallow tree is beneficial to water accumulation, insecticidal and detoxification. Existing studies have proved that XT can treat acute perforating appendicitis, infectious hepatitis and renal degeneration syndrome; XT in vivo and in vitro administration has obvious inhibitory effect and amount on collagen and platelet aggregation induced by PAF, ADP, AA and thrombin One-effect relationship; XT and its derivatives have the effects of deworming and stopping roundworms, bactericidal, anti-microbial, and anti-mold....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/84C07C45/64
Inventor 杨健吴婷杨涛杨波吴远双
Owner KUNMING UNIV OF SCI & TECH
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