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Novel synthesis method of sesamol

A new synthesis technology of sesamol, which is applied in the field of new synthesis of sesamol, can solve the problems of reducing product coloring, separation difficulties, and low product purity, and achieves the effects of low equipment requirements, low dosage, and low production cost

Inactive Publication Date: 2018-11-02
SUZHOU GAIDE FINE MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Chinese patent (200510036476.1) discloses a synthetic method of natural food antioxidant sesamol, which uses piperonylamine as a synthetic precursor to synthesize natural structure antioxidant sesamol through diazotization and hydrolysis reactions, and selects non-water-soluble Organic solvents, especially benzene-based organic solvents, are used as suitable extractants for hydrolysis products, which greatly reduces product coloring and increases yields. The steps are simple, but the product has low purity and is difficult to separate

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The new synthetic method of sesamol, comprises the following steps:

[0028] (1) Dissolve γ-glycidyloxypropyltrimethoxysilane in absolute ethanol to obtain a modified solution, then add mullite powder, ultrasonically treat for 30 minutes at a power of 500W, and filter to obtain The precipitate was redispersed in n-hexane solution containing triethylbenzyl ammonium chloride, slowly heated to 50-60°C, stirred at 1500rpm for 1h, cooled to room temperature after the treatment, filtered, and the obtained precipitate was dried. Prepare a supported catalyst; wherein, the mass ratio of the gamma-glycidyloxypropyltrimethoxysilane, mullite powder, and triethylbenzyl ammonium chloride is 0.01:5:0.1;

[0029] (2) Dissolving catechol in DMF, adding dichloromethane, adding the supported catalyst prepared above, and reacting at 100-105 ° C, after the reaction, piperonyl ring is obtained; wherein, the o-phenyl The mass ratio of diphenol and dichloromethane is 5:1; the mass ratio of th...

Embodiment 2

[0034] The new synthetic method of sesamol, comprises the following steps:

[0035] (1) Dissolve γ-glycidyloxypropyltrimethoxysilane in absolute ethanol to obtain a modified solution, then add mullite powder, ultrasonically treat for 30 minutes at a power of 1000W, and filter to obtain The precipitate was redispersed in n-hexane solution containing triethylbenzyl ammonium chloride, slowly heated to 50-60°C, stirred at a speed of 5000rpm for 5h, cooled to room temperature after the treatment, filtered, and the obtained precipitate was dried. Prepare a supported catalyst; wherein, the mass ratio of the gamma-glycidyloxypropyltrimethoxysilane, mullite powder, and triethylbenzyl ammonium chloride is 0.03:5:0.1;

[0036] (2) Dissolving catechol in DMF, adding dichloromethane, adding the supported catalyst prepared above, and reacting at 100-105 ° C, after the reaction, piperonyl ring is obtained; wherein, the o-phenyl The mass ratio of diphenol and dichloromethane is 5:2; the mass...

Embodiment 3

[0041] The new synthetic method of sesamol, comprises the following steps:

[0042] (1) Dissolve γ-glycidyloxypropyltrimethoxysilane in absolute ethanol to obtain a modified solution, then add mullite powder, ultrasonically treat for 30 minutes at a power of 600W, and filter to obtain The precipitate was redispersed in n-hexane solution containing triethylbenzyl ammonium chloride, slowly heated to 50-60°C, stirred at a speed of 2000rpm for 2h, cooled to room temperature after the treatment, filtered, and the obtained precipitate was dried. A supported catalyst is obtained; wherein, the mass ratio of the gamma-glycidyloxypropyltrimethoxysilane, mullite powder, and triethylbenzyl ammonium chloride is 0.015:5:0.1;

[0043] (2) Dissolving catechol in DMF, adding dichloromethane, adding the supported catalyst prepared above, and reacting at 100-105 ° C, after the reaction, piperonyl ring is obtained; wherein, the o-phenyl The mass ratio of diphenol and dichloromethane is 5:1.2; th...

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PUM

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Abstract

The invention discloses a novel synthesis method of sesamol. The method specifically comprises the following steps: first, gamma-glycidyl oxypropyl trimethoxysilane is used as a dispersing agent to prepare modified mullite powder; then, the modified mullite powder is used as a carrier to prepare a supported catalyst; catechol and dichloromethane are used as raw materials to prepare 1,3-benzodioxole under the catalysis of the supported catalyst; glyoxylic acid, a sulfuric acid solution and 1,3-benzodioxole are used as raw materials to obtain 3,4-methylenedioxy phenyl glycolic acid; the 3,4-methylenedioxy phenyl glycolic acid reacts with a nitric acid solution to prepare piperonal; finally, the piperonal and MCPBA react to prepare the sesamol. The method disclosed in the invention is simpleto operate, low in preparation cost and high in product yield.

Description

Technical field: [0001] The invention relates to the field of organic preparation, in particular to a new synthesis method of sesamol. Background technique: [0002] Sesamol, whose chemical name is 3,4-methylenedioxyphenol, is extracted and separated from sesame oil. It is the main aroma component and quality stabilizer of sesame oil. It has strong antibacterial and antioxidant activities, and is an excellent low-toxicity antioxidant. At the same time, due to its unique molecular structure and significant pharmacological activity, it has become a synthetic drug for treating hypertension, tumors, coronary heart disease, and senile depression. [0003] There are three main synthetic techniques of sesamol: one is extraction from sesame oil, the other is total synthesis with piperonamine, and the third is semi-synthetic route from jasmonal. Extracting sesamol from sesame oil requires large solvent consumption and high cost, and is not suitable for industrialized production; th...

Claims

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Application Information

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IPC IPC(8): C07D317/64
CPCC07D317/64
Inventor 李晓明
Owner SUZHOU GAIDE FINE MATERIALS CO LTD
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