CN102911031A - Synthetic process for flavonoid compound intermediate - Google Patents
Synthetic process for flavonoid compound intermediate Download PDFInfo
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- CN102911031A CN102911031A CN 201110221254 CN201110221254A CN102911031A CN 102911031 A CN102911031 A CN 102911031A CN 201110221254 CN201110221254 CN 201110221254 CN 201110221254 A CN201110221254 A CN 201110221254A CN 102911031 A CN102911031 A CN 102911031A
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- compound intermediate
- flavonoid compound
- synthetic process
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- JECYUBVRTQDVAT-UHFFFAOYSA-N CC(c1ccccc1O)=O Chemical compound CC(c1ccccc1O)=O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 description 1
- AETKQQBRKSELEL-ZHACJKMWSA-N Oc(cccc1)c1C(/C=C/c1ccccc1)=O Chemical compound Oc(cccc1)c1C(/C=C/c1ccccc1)=O AETKQQBRKSELEL-ZHACJKMWSA-N 0.000 description 1
Abstract
The invention provides relates to a synthetic process for a compound intermediate, in particular to a synthetic process for a flavonoid compound intermediate. The invention provides the synthetic process for the flavonoid compound intermediate, which is featured by high extraction rate and is suitable for industrial production. According to the invention, the following technical scheme is adopted: under the catalysis of dilute alkali, chalcone is synthesized through aldol condensation reaction; and the steps of the process are as follows: adding 95 % of ethanol and 10-20 % of aqueous alkali to a three-opening bottle; adding benzaldehyde and hydroxyacetophenone to the three-opening bottle in sequence at 20 DEG C; reacting the materials for 19-20 h at 15-30 DEG C; after the reaction is finished, slowly dripping glacial acetic acid to a reactant in ice-water bath so as to adjust the pH value of a system to 6-6.5; filtering the reactant; concentrating a filter liquor; recycling ethanol; stirring and washing a wet solid by ice water for 2-3 times; and filtering and drying the wet solid so as to obtain a finished product.
Description
Technical field:
The present invention relates to the synthesis technique of compound intermediate, more particularly, relate to the synthesis technique of flavonoid compound intermediate.
Background technology:
Flavonoid compound is a class natural product that extensively is present in the vegitabilia, and its physiologically active is extensive, comprises anti-cardiovascular disease activity, anti-inflammatory activity, anti-liver virus, antibiotic isoreactivity.Phenyl styryl ketone as its family's a member also has anti-tumor activity.Phenyl styryl ketone or a kind of important organic synthesis intermediate can be used for the synthetic of the fine chemicals such as spices and medicine.
The synthetic method that phenyl styryl ketone is commonly used is to use the aldol condensation of strong acid or highly basic catalysis methyl phenyl ketone and phenyl aldehyde, but side reaction is more, and productive rate is on the low side, how 50%～70%; Also have organic tellurium oxide compound of use to make catalyzer, really obtained preferably effect, but the preparation of this catalyzer is difficult, expensive; Use in addition ultrasonic wave, solid phase synthesis and microwave method, but these methods all are unsuitable for industrialization.
Summary of the invention:
The present invention is exactly for the problems referred to above, provides that a kind of extraction yield is high, the synthesis technique of the flavonoid compound intermediate that is applicable to suitability for industrialized production.
In order to realize above-mentioned purpose of the present invention, the present invention adopts following technical scheme, under diluted alkaline catalysis, synthesized phenyl styryl ketone by aldol reaction, processing step is: the ethanol with 95% and 10～20% alkaline solution add in the there-necked flask, under 20 ℃, add successively phenyl aldehyde, o-hydroxyacetophenone, under 15～30 ℃, reaction 19～20h; Reaction slowly drips Glacial acetic acid after finishing in ice-water bath, the pH value of regulation system is 6～6.5; Filter, filtrate is concentrated, and ethanol reclaims; Wet solid stirs with frozen water washes 2～3 times, filters, dries, and obtains finished product.
Reaction equation is:
Beneficial effect of the present invention:
1. the present invention is simple to operate, and ethanol can recycle, and is beneficial to large-scale industrial production;
2. productive rate of the present invention is 88.4%.
Embodiment:
Processing step of the present invention is: the ethanol with 95% and 10～20% alkaline solution add in the there-necked flask, add successively phenyl aldehyde, o-hydroxyacetophenone under 20 ℃, under 15～30 ℃, and reaction 19～20h; Reaction slowly drips Glacial acetic acid after finishing in ice-water bath, the pH value of regulation system is 6～6.5; Filter, filtrate is concentrated, and ethanol reclaims; Wet solid stirs with frozen water washes 2～3 times, filters, dries, and obtains finished product.
Reaction equation is:
As a kind of preferred version, processing step of the present invention is: alkaline solution is 12% NaOH, and temperature of reaction is 20～25 ℃.
Claims (2)
1. the synthesis technique of flavonoid compound intermediate, it is characterized in that, the present invention adopts following technical scheme, under diluted alkaline catalysis, synthesized phenyl styryl ketone by aldol reaction, processing step is: the ethanol with 95% and 10～20% alkaline solution add in the there-necked flask, under 20 ℃, add successively phenyl aldehyde, o-hydroxyacetophenone, under 15～30 ℃, reaction 19～20h; Reaction slowly drips Glacial acetic acid after finishing in ice-water bath, the pH value of regulation system is 6～6.5; Filter, filtrate is concentrated, and ethanol reclaims; Wet solid stirs with frozen water washes 2～3 times, filters, dries, and obtains finished product.
Reaction equation is:
2. the synthesis technique of flavonoid compound intermediate according to claim 1 is characterized in that, processing step of the present invention is: alkaline solution is 12% NaOH, and temperature of reaction is 20～25 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201110221254 CN102911031A (en) | 2011-08-04 | 2011-08-04 | Synthetic process for flavonoid compound intermediate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201110221254 CN102911031A (en) | 2011-08-04 | 2011-08-04 | Synthetic process for flavonoid compound intermediate |
Publications (1)
| Publication Number | Publication Date |
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| CN102911031A true CN102911031A (en) | 2013-02-06 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| CN 201110221254 Pending CN102911031A (en) | 2011-08-04 | 2011-08-04 | Synthetic process for flavonoid compound intermediate |
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| CN (1) | CN102911031A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103641704A (en) * | 2013-12-18 | 2014-03-19 | 福建省永安市智源生化有限公司 | Method for preparing phenylacetic acid derivative |
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2011
- 2011-08-04 CN CN 201110221254 patent/CN102911031A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103641704A (en) * | 2013-12-18 | 2014-03-19 | 福建省永安市智源生化有限公司 | Method for preparing phenylacetic acid derivative |
| CN103641704B (en) * | 2013-12-18 | 2015-08-26 | 福建省永安市智源生化有限公司 | A kind of method preparing phenylacetic acid derivatives |
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Legal Events
| Date | Code | Title | Description |
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| C06 | Publication | ||
| PB01 | Publication | ||
| DD01 | Delivery of document by public notice |
Addressee: Wen Hao Document name: Notification of Publication of the Application for Invention |
|
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20130206 |