CN105693477A - Synthesis method of trimethoxystilbene - Google Patents
Synthesis method of trimethoxystilbene Download PDFInfo
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- CN105693477A CN105693477A CN201610169675.8A CN201610169675A CN105693477A CN 105693477 A CN105693477 A CN 105693477A CN 201610169675 A CN201610169675 A CN 201610169675A CN 105693477 A CN105693477 A CN 105693477A
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- resveratrol
- methyl ether
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a synthesis method of trimethoxystilbene. The method comprises the following steps of (1) at room temperature, adding trifluoromethanesulfonic acid into dichloromethane; stirring the mixture; slowly dripping sulfoxide chloride; after the dripping is completed, performing stirring reaction for 12 hours at room temperature; concentrating a reaction system to obtain a coarse product of trifluoromethanesulfonyl chloride; (2) adding aniline and triethylamine into dichloromethane; lowering the temperature to 0 DEG C; dripping the obtained coarse product of trifluoromethanesulfonyl chloride through a dropping funnel; after the dripping is completed, raising the temperature to room temperature for reaction for 2 hours; performing water washing, drying and concentration on the reaction system; then, performing recrystallization by petroleum ether to obtain trimethoxystilbene. The synthesis method has the beneficial effects that the raw materials of trifluoromethanesulfonic acid used by the synthesis method of trimethoxystilbene provided by the invention are common chemical raw materials; the price is low; the acquisition is easy; the cost is greatly reduced; special equipment such as low-temperature kettles is not needed in the production process; the operation is easy; the method is suitable for industrial production.
Description
Technical field
The present invention relates to compou nd synthesis technical field, be specifically related to the synthetic method of a kind of resveratrol three methyl ether。
Background technology
Resveratrol three methyl ether is the important synthesis material of a lot of antimicrobial drug, appetrol, cancer therapy drug and adjuvant。Such as prepare and there are the H-PGDS inhibitor of antitumaous effect, Rho-inhibitors of kinases, KSP inhibitor, CSF-1R inhibitor, renin inhibitor etc.。In the last few years a series of be key intermediate with this compounds new drug be found, the demand of such intermediate is increased by market day by day。But by the investigation to existing market, large-scale Reagent Company of domestic only several families provides gram level fractional pack of reagent grade at present, there is no any unit and can provide this product in bulk。
It is currently known the synthetic method of resveratrol three methyl ether that large-scale corporation de facto of a few family of Cunninghamia lanceolata (Lamb.) Hook. can be provided by, is all with trifluoromethanesulfanhydride anhydride for raw material, in subzero 80 degree of reactions, process to obtain product。Raw material trifluoromethanesulfanhydride anhydride used by the method is expensive, and is all import；Needing in production to use subzero 80 degree of low-temp reaction stills, the method cost is high, equipment requirements is high, not easily operate, be difficult to amplification produces。
Summary of the invention
The purpose of the present invention is aiming at above-mentioned defect of the prior art, it is provided that a kind of cost is low, without special installation, easily operate and be suitable to the synthetic method of resveratrol three methyl ether of industrialized production。
To achieve these goals, technical scheme provided by the invention is: the synthetic method of a kind of resveratrol three methyl ether, comprises the following steps:
1) under room temperature, the trifluoromethanesulfonic acid of 1mol is added in the dichloromethane of 1L, stir and be slowly added dropwise the thionyl chloride of 0.5-1.5mol, control time 55-65min and dropwise, reaction 12 hour is stirred at room temperature, reaction system is concentrated to obtain crude product trifluoromethanesulfchloride chloride；
2) triethylamine of the aniline of 1mol, 0.5-1.5mol is joined in the dichloromethane of 1L, it is cooled to 0 DEG C, the crude product trifluoromethanesulfchloride chloride 0.5-1.5mol that step 1) is obtained is dripped by Dropping funnel, it is warming up to room temperature reaction after dropwising 2 hours, reaction system is obtained resveratrol three methyl ether with petroleum ether recrystallization after washing, dry, concentrating。
The process of reaction is as shown in Figure 1。
Further, the synthetic method of above-mentioned a kind of resveratrol three methyl ether, in described step 1), the addition of thionyl chloride is 1mol。
Further, the synthetic method of above-mentioned a kind of resveratrol three methyl ether, in described step 1), the time for adding of thionyl chloride is 60min。
Further, the synthetic method of above-mentioned a kind of resveratrol three methyl ether, described step 2) in, the addition of triethylamine is 1mol。
Further, the synthetic method of above-mentioned a kind of resveratrol three methyl ether, described step 2) in, the dripping quantity of product trifluoromethanesulfchloride chloride is 1mol。
The invention have the benefit that the synthetic method of a kind of resveratrol three methyl ether provided by the invention, its raw materials used trifluoromethanesulfonic acid, for common industrial chemicals, cheap and easy to get, greatly reduce cost, and production process does not need the special installations such as low temperature still, it is easy to and operation, be suitable to industrialized production。
Accompanying drawing explanation
Fig. 1 is the reaction scheme schematic diagram of the synthetic method of a kind of resveratrol three methyl ether provided by the invention。
Detailed description of the invention
Embodiment 1:
A kind of synthetic method of resveratrol three methyl ether, the process of reaction is as it is shown in figure 1, comprise the following steps:
1) under room temperature, the trifluoromethanesulfonic acid of 1mol is added in the dichloromethane of 1L, stir and be slowly added dropwise the thionyl chloride of 0.5mol, the control time, 55min dropwised, reaction 12 hour is stirred at room temperature, reaction system is concentrated to obtain crude product trifluoromethanesulfchloride chloride, it is not necessary to purification, can be directly used for next step reaction；
2) triethylamine of the aniline of 1mol, 0.5mol is joined in the dichloromethane of 1L, it is cooled to 0 DEG C, the crude product trifluoromethanesulfchloride chloride 0.5mol that step 1) is obtained is dripped by Dropping funnel, it is warming up to room temperature reaction after dropwising 2 hours, reaction system is obtained resveratrol three methyl ether with petroleum ether recrystallization after washing, dry, concentrating。
Embodiment 2:
A kind of synthetic method of resveratrol three methyl ether, the process of reaction is as it is shown in figure 1, comprise the following steps:
1) under room temperature, the trifluoromethanesulfonic acid of 1mol is added in the dichloromethane of 1L, stir and be slowly added dropwise the thionyl chloride of 1.5mol, the control time, 65min dropwised, reaction 12 hour is stirred at room temperature, reaction system is concentrated to obtain crude product trifluoromethanesulfchloride chloride, it is not necessary to purification, can be directly used for next step reaction；
2) triethylamine of the aniline of 1mol, 1.5mol is joined in the dichloromethane of 1L, it is cooled to 0 DEG C, the crude product trifluoromethanesulfchloride chloride 1.5mol that step 1) is obtained is dripped by Dropping funnel, it is warming up to room temperature reaction after dropwising 2 hours, reaction system is obtained resveratrol three methyl ether with petroleum ether recrystallization after washing, dry, concentrating。
Embodiment 3:
A kind of synthetic method of resveratrol three methyl ether, the process of reaction is as it is shown in figure 1, comprise the following steps:
1), under room temperature, the trifluoromethanesulfonic acid of 1mol is added in the dichloromethane of 1L, stir and be slowly added dropwise the thionyl chloride of 1mol, the control time, 60min dropwised, and reaction 12 hour is stirred at room temperature, reaction system concentrates to obtain crude product trifluoromethanesulfchloride chloride, without purification, can be directly used for next step reaction；
2) triethylamine of the aniline of 1mol, 1mol is joined in the dichloromethane of 1L, it is cooled to 0 DEG C, the crude product trifluoromethanesulfchloride chloride 1mol that step 1) is obtained is dripped by Dropping funnel, it is warming up to room temperature reaction after dropwising 2 hours, reaction system is obtained resveratrol three methyl ether with petroleum ether recrystallization after washing, dry, concentrating。
Last it is noted that the foregoing is only the preferred embodiments of the present invention, it is not limited to the present invention, although the present invention being described in detail with reference to previous embodiment, for a person skilled in the art, technical scheme described in foregoing embodiments still can be modified by it, or wherein portion of techniques feature carries out equivalent replacement。All within the spirit and principles in the present invention, any amendment of making, equivalent replacement, improvement etc., should be included within protection scope of the present invention。
Claims (5)
1. the synthetic method of resveratrol three methyl ether, it is characterised in that comprise the following steps:
1) under room temperature, the trifluoromethanesulfonic acid of 1mol is added in the dichloromethane of 1L, stir and be slowly added dropwise the thionyl chloride of 0.5-1.5mol, control time 55-65min and dropwise, reaction 12 hour is stirred at room temperature, reaction system is concentrated to obtain crude product trifluoromethanesulfchloride chloride；
2) triethylamine of the aniline of 1mol, 0.5-1.5mol is joined in the dichloromethane of 1L, it is cooled to 0 DEG C, the crude product trifluoromethanesulfchloride chloride 0.5-1.5mol that step 1) is obtained is dripped by Dropping funnel, it is warming up to room temperature reaction after dropwising 2 hours, reaction system is obtained resveratrol three methyl ether with petroleum ether recrystallization after washing, dry, concentrating。
2. the synthetic method of a kind of resveratrol three methyl ether according to claim 1, it is characterised in that in described step 1), the addition of thionyl chloride is 1mol。
3. the synthetic method of a kind of resveratrol three methyl ether according to claim 1, it is characterised in that in described step 1), the time for adding of thionyl chloride is 60min。
4. the synthetic method of a kind of resveratrol three methyl ether according to claim 1, it is characterised in that described step 2) in, the addition of triethylamine is 1mol。
5. the synthetic method of a kind of resveratrol three methyl ether according to claim 1, it is characterised in that described step 2) in, the dripping quantity of product trifluoromethanesulfchloride chloride is 1mol。
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610169675.8A CN105693477A (en) | 2016-03-23 | 2016-03-23 | Synthesis method of trimethoxystilbene |
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| CN201610169675.8A CN105693477A (en) | 2016-03-23 | 2016-03-23 | Synthesis method of trimethoxystilbene |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110627691A (en) * | 2019-08-20 | 2019-12-31 | 中船重工（邯郸）派瑞特种气体有限公司 | Method for preparing N-phenyl-bis (perfluoroalkyl sulfonyl) imine |
| CN112830887A (en) * | 2020-12-30 | 2021-05-25 | 中船重工（邯郸）派瑞特种气体有限公司 | Preparation method of N-phenyl bis (trifluoromethanesulfonyl) imide |
| CN113735693A (en) * | 2021-10-20 | 2021-12-03 | 河北维达康生物科技有限公司 | Synthesis method of resveratrol monomethyl ether |
| CN115724774A (en) * | 2022-12-16 | 2023-03-03 | 山东华安新材料有限公司 | Preparation method of trifluoromethyl sulfonyl chloride |
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| EP1016655A2 (en) * | 1998-12-28 | 2000-07-05 | Central Glass Company, Limited | Method for producing trifluoromethanesulfonyl chloride |
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| JP2003286244A (en) * | 2002-03-27 | 2003-10-10 | Yakult Honsha Co Ltd | Method for producing n-phenyl- bis(trifluoromethanesulfonimide) |
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| JP2003286244A (en) * | 2002-03-27 | 2003-10-10 | Yakult Honsha Co Ltd | Method for producing n-phenyl- bis(trifluoromethanesulfonimide) |
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| JP2009102294A (en) * | 2007-10-02 | 2009-05-14 | Central Glass Co Ltd | Method for purification of trifluoromethanesulfonyl fluoride |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110627691A (en) * | 2019-08-20 | 2019-12-31 | 中船重工（邯郸）派瑞特种气体有限公司 | Method for preparing N-phenyl-bis (perfluoroalkyl sulfonyl) imine |
| CN110627691B (en) * | 2019-08-20 | 2022-03-25 | 中船(邯郸)派瑞特种气体股份有限公司 | Method for preparing N-phenyl-bis (perfluoroalkyl sulfonyl) imine |
| CN112830887A (en) * | 2020-12-30 | 2021-05-25 | 中船重工（邯郸）派瑞特种气体有限公司 | Preparation method of N-phenyl bis (trifluoromethanesulfonyl) imide |
| CN113735693A (en) * | 2021-10-20 | 2021-12-03 | 河北维达康生物科技有限公司 | Synthesis method of resveratrol monomethyl ether |
| CN115724774A (en) * | 2022-12-16 | 2023-03-03 | 山东华安新材料有限公司 | Preparation method of trifluoromethyl sulfonyl chloride |
| CN115724774B (en) * | 2022-12-16 | 2023-12-26 | 山东华安新材料有限公司 | Preparation method of trifluoromethyl sulfonyl chloride |
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