CN107324985A - A kind of preparation method of beta-diketone compound - Google Patents
A kind of preparation method of beta-diketone compound Download PDFInfo
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- C07—ORGANIC CHEMISTRY
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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Abstract
The present invention relates to field of compound preparation, a kind of preparation method of beta diketone compound is disclosed, wherein, this method includes：In the presence of solvent of the present invention and alkali metal potassium alcoholate, carboxylate methyl ester is reacted with ketone.The method high income of the present invention for preparing beta diketone compound, safety is adapted to commercial Application.3, during 5 heptadione are prepared in particular by the method for the invention, the yield of 3,5 heptadione reaches more than 60%, and yield is far above the yield for preparing 3,5 heptadione by solvent of DMF in the prior art.
Description
Technical field
The present invention relates to field of compound preparation, in particular it relates to a kind of preparation side of beta-diketone compound
Method.
Background technology
Beta-diketone compound is the compound that a class has special construction, is widely used in catalyst, thermally-stabilised
The field such as agent and luminescent material.
It is well known that ester ketone condensation method is to prepare beta-diketone compound common method.For example, periodical literature
J.Org.chem (Vol.50.No26.1985.5598-5604) is reported, in the presence of sodium hydride, with tetrahydrochysene
Furans is solvent, and ethyl propionate and the first and second reactive ketones prepare 3,5- heptadione, and yield is 48.3%.
Periodical literature Zhurnal Obshchei Khimii (1958,28,2845~2846) in, use
Malonyl chloride and grignard reagent E tMgBr reaction synthesis 3,5- heptadione, yield is 51%.React bar
Part is -70 DEG C, and is difficult to handle, therefore industrialized difficulty is very big.
In summary, in existing technologies, also without safety, beta-diketone compound is prepared in high yield
Method.
The content of the invention
The purpose of the present invention be overcome prior art prepare beta-diketone compound yield it is low and unsafe
There is provided a kind of preparation method of beta-diketone compound for defect.
To achieve these goals, the invention provides the beta-diketone compound shown in a kind of formula (4)
Preparation method, wherein, this method includes：In the presence of solvent and alkali metal potassium alcoholate shown in formula (3)
Under, the carboxylate methyl ester shown in formula (1) is reacted with the ketone shown in formula (2)；
CH3O-CO-CR1R2R3Formula (1)；
CH3-CO-CR1R2R3Formula (2)；
R4O-(CH2(CH2)nO)m-R4Formula (3)；
R3R2R1C-CO-CH2-CO-CR1R2R3Formula (4)；
Wherein, R1、R2And R3It is each independently hydrogen or C1-C4Alkyl；
Wherein, n and m are identical or different, and n and m are each independently selected from 1,2 or 3；R4For first
Base or ethyl.
The method high income of the present invention for preparing beta-diketone compound, safety is adapted to commercial Application.
When preparing 3,5- heptadione in particular by the method for the invention, the yield of 3,5- heptadione reaches 60%
More than, yield is far above the yield for preparing 3,5- heptadione by solvent of DMF in the prior art.
Other features and advantages of the present invention will be described in detail in subsequent embodiment part.
Embodiment
The embodiment to the present invention is described in detail below.It should be appreciated that this place is retouched
The embodiment stated is merely to illustrate and explain the present invention, and is not intended to limit the invention.
The end points and any value of disclosed scope are not limited to the accurate scope or value herein, this
A little scopes or value should be understood to comprising the value close to these scopes or value.For number range, respectively
Between the endpoint value of individual scope, between the endpoint value of each scope and single point value, and individually point
Can be combined with each other between value and obtain one or more new number ranges, these number ranges should by regarding
For specific disclosure herein.
The invention provides the preparation method of the beta-diketone compound shown in a kind of formula (4), wherein, should
Method includes：In the presence of the solvent and alkali metal potassium alcoholate shown in formula (3), by shown in formula (1)
Carboxylate methyl ester is reacted with the ketone shown in formula (2)；
CH3O-CO-CR1R2R3Formula (1)；
CH3-CO-CR1R2R3Formula (2)；
R4O-(CH2(CH2)nO)m-R4Formula (3)；
R3R2R1C-CO-CH2-CO-CR1R2R3Formula (4)；
Wherein, R1、R2And R3It is each independently hydrogen or C1-C4Alkyl, such as R1、R2And R3
It can be each independently hydrogen, methyl, ethyl, n-propyl, isopropyl, it is normal-butyl, sec-butyl, different
One kind in butyl and the tert-butyl group；Preferably, R1、R2And R3It is each independently hydrogen or C1-C2Alkane
Base, for example, can be each independently hydrogen, methyl or ethyl；It is highly preferred that the carboxylic shown in formula (1)
Sour methyl esters is methyl propionate, and the ketone shown in formula (2) is butanone.
In formula (3), n and m are identical or different, and n and m are each independently selected from 1,2 or 3；
Preferably, n and m are 1；Or n is that 1, m is 2 or 3；It is highly preferred that n is for 1, m
2。
In formula (3), R4For methyl or ethyl, preferably methyl.
In the case of most preferably, the solvent shown in formula (3) is diethylene glycol dimethyl ether.
In the present invention, to the consumption of the solvent, there is no particular limitation, as long as stirring reaction can be reached
System.But in order to improve under reaction efficiency, preferable case, the consumption of the solvent and the ketone
Consumption mol ratio be 0.9-5：1, preferably 1-4：1, more preferably 0.97-3：1.
In the present invention, the effect of the alkali metal potassium alcoholate is the compatibility for the α carbon for improving the ketone, makes acyl
Change reaction to be easier to make for.There is no particular limitation for consumption of the present invention to the alkali metal potassium alcoholate, as long as
Reaction can be smoothed out.But, if the consumption of the alkali metal potassium alcoholate is very few, cause anti-
Effect is answered to be deteriorated；If the consumption of the alkali metal potassium alcoholate is excessive, side reaction can be caused and yield is reduced.
It is therefore preferable that in the case of, the mol ratio of the consumption and the consumption of the ketone of the alkali metal potassium alcoholate is
1-1.25：1, more preferably 1-1.2：1, more preferably 1-1.1：1.
In the present invention, to the selection of the alkali metal potassium alcoholate, there is no particular limitation, can be conventional for ability
Selection, can be for example potassium methoxide, potassium ethoxide, normal propyl alcohol potassium, potassium isopropoxide, n-butanol potassium, different
At least one of butanol potassium, sec-butyl alcohol potassium and potassium tert-butoxide；Preferably, the alkali metal potassium alcoholate is first
At least one of potassium alcoholate, potassium ethoxide and potassium tert-butoxide.
In the present invention, to the consumption of the carboxylate methyl ester, there is no particular limitation, can be conventional for this area
Selection.But, can be by institute if the consumption of the ketone is much larger than the consumption of the carboxylate methyl ester
State the influence self condensed of ketone and reduce target product yield；If the consumption of the carboxylate methyl ester is much larger than
The consumption of the ketone, then must recycle a large amount of unreacted carboxylate methyl esters.It is therefore preferable that in the case of,
The mol ratio of the consumption of the carboxylate methyl ester and the consumption of the ketone is 3-10：1, preferably 3-4.1：1.
In the present invention, to the condition of the reaction, there is no particular limitation, can be the conventional bar in this area
Part.But, if reaction temperature is too low, reactivity is deteriorated and the reaction time extends, so as to cause life
Production capacity power declines；If reaction temperature is too high, waste and the more pairs of solvent and reactant can be caused
Reaction occurs and reduces product yield.It is therefore preferable that in the case of, the condition of the reaction includes：Temperature
For 0-100 DEG C, preferably 60-75 DEG C；Time is 2-6h, preferably 4-5h.
In the present invention, to the Adding Way of reactant, there is no particular limitation, can be the routine of this area
Method.Under preferable case, first the solvent and the alkali metal potassium alcoholate are mixed, mixture is obtained, so
The mixed liquor of the carboxylate methyl ester and the ketone is added drop-wise in the mixture afterwards.Under preferable case, institute
The time for stating dropwise addition is 10-60min, more preferably 20-40min.In the present invention, " dropwise addition " refers to
The mixed liquor is substantially evenly instilled in the mixture in the given time.
In the present invention, methods described can also include：After the reaction terminates, by formula (4) institute
The beta-diketone compound shown is separated from reaction product.Specifically, added water into reaction product, Ran Houtong
It is 6-7 to cross concentrated hydrochloric acid regulation pH, is cooled to after room temperature, first passes through and be separated by filtration inorganic salts, then
Separate organic layer and water layer, rectifying purifying finally carried out to organic layer, by unreacted raw material, solvent and
Other impurities are separated.
The present invention will be described in detail by way of examples below.
In following examples and comparative example, beta-diketone compound is quantitative determined using GC-External Standard method；
The computational methods of yield in following examples and comparative example：
Beta-diketone compound yield=(beta-diketone compound generates the mole of mole/ketone reactant) ×
100%
Embodiment 1
135g (1.2mol) potassium tert-butoxide is added in 1 liter of four-hole boiling flask (purchased from Chinese medicines group chemistry examination
Agent Co., Ltd, referred to as " traditional Chinese medicines company ", similarly hereinafter) and 104.5g (1.16mol) glycol dimethyl ether
(being purchased from traditional Chinese medicines company), is heated to reflux being warming up to 20 DEG C under mechanical agitator stirring.Then, pass through
Constant pressure funnel at the uniform velocity add by 319g (3.6mol) methyl propionate (be purchased from TCI companies of Japan) and
The liquid mixture of 86.5g (1.2mol) butanone (being purchased from traditional Chinese medicines company) composition, time for adding is 20min,
Then it is stirred at 75 DEG C 4.5 hours, cools to 40 DEG C, is added 120g frozen water, adjusted with concentrated hydrochloric acid
Save pH to 6.Then filtered with bottle,suction, remove potassium chloride, filtrate layered separates organic layer and water
Layer.By carrying out gas chromatographic analysis to organic layer, the 3,5- of 103g (0.80mol) are generated
Heptadione, yield is 66.6% (in terms of butanone).
Embodiment 2
13.6g (0.12mol) potassium tert-butoxide (being purchased from traditional Chinese medicines company) is added in 250ml three-necked flasks
With 40mL (0.28mol) diethylene glycol dimethyl ether, it is heated to reflux being warming up under mechanical agitator stirring
60℃.Then, at the uniform velocity added by constant pressure funnel by the (purchase of 39mL (0.41mol) methyl propionate
From Japanese TCI companies) and 9mL (0.1mol) butanone (be purchased from traditional Chinese medicines company) composition liquid mixing
Thing, time for adding is 40min, is then stirred at 60 DEG C 4.5 hours, cools to 40 DEG C, addition
20g frozen water, pH to 6 is adjusted with concentrated hydrochloric acid.Then filtered with bottle,suction, remove potassium chloride, filtrate point
Layer, separates organic layer and water layer.By carrying out gas chromatographic analysis, 3,5- heptadione to organic layer
Yield be 64.3% (in terms of butanone).
Embodiment 3
148g (1.32mol) potassium tert-butoxide (traditional Chinese medicines company) and 324.4g are added in 1 liter of four-hole boiling flask
(3.6mol) glycol dimethyl ether (is purchased from traditional Chinese medicines company), is heated to reflux under mechanical agitator stirring
It is warming up to 20 DEG C.Then, at the uniform velocity added by constant pressure funnel by 370g (4.2mol) propionic acid first
What ester (being purchased from TCI companies of Japan) and 86.5g (1.2mol) butanone (being purchased from traditional Chinese medicines company) were constituted
Liquid mixture, time for adding is 30min, is then stirred at 65 DEG C 4.5 hours, cools to 40 DEG C,
120g frozen water is added, pH to 6 is adjusted with concentrated hydrochloric acid.Then filtered with bottle,suction, remove potassium chloride,
Filtrate layered, separates organic layer and water layer.By carrying out gas chromatographic analysis, 3,5- to organic layer
The yield of heptadione is 62.2% (in terms of butanone).
Embodiment 4
27.2g (0.24mol) potassium tert-butoxide (being purchased from traditional Chinese medicines company) is added in 250ml three-necked flasks
With the dimethylamino ethanol ethers of 43ml (0.24mol) three (be purchased from Aladdin company), 69ml is at the uniform velocity added dropwise at 60 DEG C
(0.72mol) methyl propionate and 21.5ml (0.24mol) butanone, time for adding 40min, Ran Hou
It is stirred at 75 DEG C 4.5 hours, cools to 40 DEG C, add 24g frozen water, is arrived with concentrated hydrochloric acid regulation pH
6.Then filtered with bottle,suction, remove potassium chloride, filtrate layered separates organic layer and water layer.Pass through
Gas chromatographic analysis is carried out to organic layer to understand, generates 19g (0.148mol) 3,5- heptadione,
Yield is 61.7% (in terms of butanone).
Embodiment 5
27.2g (0.24mol) potassium tert-butoxide (being purchased from traditional Chinese medicines company) is added in 250ml three-necked flasks
With 34ml (0.24mol) (Tianjin recovery fine chemistry industry research institute) diethyl diethylene glycol dimethyl ether, 60 DEG C of dropwise additions
69ml (0.72mol) methyl propionate (being purchased from TCI companies of Japan) and 21.5ml (0.24mol) butanone
(being purchased from traditional Chinese medicines company), then time for adding 40min is stirred for 4.5 hours at 75 DEG C, cools to
40 DEG C, 24g frozen water is added, pH to 6 is adjusted with concentrated hydrochloric acid.Then filtered with bottle,suction, remove chlorine
Change potassium, filtrate layered separates organic layer and water layer.By carrying out gas chromatographic analysis to organic layer,
18.8g (0.146mol) 3,5- heptadione is generated, yield is 60.8% (in terms of butanone).
Embodiment 6
According to embodiment 1 method prepare 3,5- heptadione, unlike, by embodiment 1 " then
It is stirred at 75 DEG C 4.5 hours ", it is changed into " and then being stirred at 60 DEG C 4.5 hours ".Pass through gas phase
Chromatogram confirm in the solution produce 92.7g (0.72mol) 3,5- heptadione, yield be 60.3% (with
Butanone meter).
Comparative example 1
3,5- heptadione is prepared according to the method for embodiment 1, unlike, add in 1 liter of four-hole boiling flask
Enter 1.2mol sodium hydrides (50%) and 1.2mol tetrahydrofurans.By carrying out gas-chromatography to organic layer
Analysis understands that the yield of 3,5- heptadione is 50% (in terms of butanone).
Comparative example 2
3,5- heptadione is prepared according to the method for embodiment 1, unlike, add in 1 liter of four-hole boiling flask
Enter 1.2mol potassium tert-butoxides and 1.2mol DMF, 50 DEG C are heated under mechanical agitator stirring.Pass through
Gas chromatographic analysis is carried out to organic layer to understand, the yield of 3,5- heptadione is 45% (in terms of butanone).
Comparative example 3
3,5- heptadione is prepared according to the method for embodiment 1, unlike, add in 1 liter of four-hole boiling flask
Enter 1.2mol potassium tert-butoxides and 1.2mol toluene, 60 DEG C are heated under mechanical agitator stirring.Pass through
Gas chromatographic analysis is carried out to organic layer to understand, the yield of 3,5- heptadione is 46% (in terms of butanone).
Comparative example 4
3,5- heptadione is prepared according to the method for embodiment 1, unlike, by solvent ethylene glycol dimethyl ether
(1.16mol) makes methyl propionate (1.15mol) into.By carrying out gas chromatographic analysis to organic layer,
The yield of 3,5- heptadione is 5% (in terms of butanone).
Comparative example 5
Added in 1 liter of four-hole boiling flask 281g (2.5mol) potassium tert-butoxide (be purchased from traditional Chinese medicines company) and
553g (6mol) methyl propionate (is purchased from company of TCI companies of Japan), and 70 DEG C are heated under agitation,
Then 72g (1mol) butanone (being purchased from traditional Chinese medicines company) was added in 5 hours with dropping funel, then
Continue stirring reaction 5 hours at 70 DEG C, be then down to room temperature, add 200g water, pH is adjusted with watery hydrochloric acid
To 7, reaction solution stratification separates organic layer.By carrying out gas chromatographic analysis to organic layer,
The yield of 3,5- heptadione is 30% (in terms of butanone).
Compared from comparative example 1-2 with embodiment 1-6, it is of the present invention to prepare beta-diketone compound (spy
Be not 3,5- heptadione) method in use the compound shown in formula (3) as solvent, than existing skill
Water-soluble aprotic solvent tetrahydrofuran, DMF high income are used in art.
Compared from comparative example 3 with embodiment 1-6, it is of the present invention to prepare beta-diketone compound (spy
Be not 3,5- heptadione) method in use the compound shown in formula (3) as solvent, than existing skill
The high income of water-insoluble solvent toluene is used in art.
Comparative example 4-5 is compared with embodiment 1-6, and comparative example is using reactant methyl propionate as solvent, and 3,5-
The yield of heptadione is very low.
The preferred embodiment of the present invention described in detail above, still, the present invention are not limited to above-mentioned reality
The detail in mode is applied, can be to technical side of the invention in the range of the technology design of the present invention
Case carries out a variety of simple variants, and these simple variants belong to protection scope of the present invention.
It is further to note that each particular technique described in above-mentioned embodiment is special
Levy, in the case of reconcilable, can be combined by any suitable means, in order to avoid need not
The repetition wanted, the present invention no longer separately illustrates to various possible combinations.
In addition, various embodiments of the present invention can be combined randomly, as long as its
Without prejudice to the thought of the present invention, it should equally be considered as content disclosed in this invention.
Claims (10)
1. a kind of preparation method of the beta-diketone compound shown in formula (4), it is characterised in that this method
Including：In the presence of the solvent and alkali metal potassium alcoholate shown in formula (3), by the carboxylic acid shown in formula (1)
Methyl esters is reacted with the ketone shown in formula (2)；
CH3O-CO-CR1R2R3Formula (1)；
CH3-CO-CR1R2R3Formula (2)；
R4O-(CH2(CH2)nO)m-R4Formula (3)；
R3R2R1C-CO-CH2-CO-CR1R2R3Formula (4)；
Wherein, R1、R2And R3It is each independently hydrogen or C1-C4Alkyl；
Wherein, n and m are identical or different, and n and m are each independently selected from 1,2 or 3；R4For first
Base or ethyl.
2. according to the method described in claim 1, wherein, R1、R2And R3Be each independently hydrogen or
C1-C2Alkyl；
Preferably, the carboxylate methyl ester shown in formula (1) is methyl propionate, and the ketone shown in formula (2) is butanone.
3. according to the method described in claim 1, wherein, in formula (3), n and m are 1；
Or n is that 1, m is 2 or 3；
Preferably, the solvent shown in formula (3) is glycol dimethyl ether.
4. the method according to any one in claim 1-3, wherein, the consumption of the solvent
Mol ratio with the consumption of the ketone is 0.9-5：1, preferably 1-4：1, more preferably 0.97-3：1.
5. the method according to any one in claim 1-3, wherein, the alkali metal potassium alcoholate
The mol ratio of consumption of consumption and the ketone be 1-1.25：1.
6. the method according to any one in claim 1-3, wherein, the alkali metal potassium alcoholate
For potassium methoxide, potassium ethoxide, normal propyl alcohol potassium, potassium isopropoxide, n-butanol potassium, isobutyl potassium alcoholate, sec-butyl alcohol potassium
At least one of with potassium tert-butoxide；
Preferably, the alkali metal potassium alcoholate is at least one of potassium methoxide, potassium ethoxide and potassium tert-butoxide.
7. the method according to any one in claim 1-3, wherein, the carboxylate methyl ester
The mol ratio of consumption and the consumption of the ketone is 3-10：1, preferably 3-4.1：1.
8. the method according to any one in claim 1-7, wherein, the condition of the reaction
Including：Temperature is 0-100 DEG C, preferably 60-75 DEG C；Time is 2-6h, preferably 4-5h.
9. the method according to any one in claim 1-8, wherein, methods described also includes：
First the solvent and the alkali metal potassium alcoholate are mixed, mixture is obtained, then by the carboxylate methyl ester and
The mixed liquor of the ketone is added drop-wise in the mixture；
Preferably, the time of the dropwise addition is 10-60min, more preferably 20-40min.
10. the method according to any one in claim 1-9, wherein, methods described also includes：
After the reaction terminates, the beta-diketone compound shown in formula (4) is separated from reaction product.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107879919A (en) * | 2018-01-09 | 2018-04-06 | 台州泰捷化工科技有限公司 | A kind of preparation method of the heptadione of medicine intermediate 3,5 |
| CN108002996A (en) * | 2018-01-09 | 2018-05-08 | 台州泰捷化工科技有限公司 | A kind of preparation method of medicine intermediate beta-diketone compound |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0454624A1 (en) * | 1990-04-26 | 1991-10-30 | Ciba-Geigy Ag | Process for the production of 1,3-diketones |
| EP2857427A1 (en) * | 2012-05-31 | 2015-04-08 | Tosoh Corporation | Catalyst composition for polyurethane resin production and method for producing polyurethane resin using same |
-
2016
- 2016-04-29 CN CN201610284401.3A patent/CN107324985B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0454624A1 (en) * | 1990-04-26 | 1991-10-30 | Ciba-Geigy Ag | Process for the production of 1,3-diketones |
| EP2857427A1 (en) * | 2012-05-31 | 2015-04-08 | Tosoh Corporation | Catalyst composition for polyurethane resin production and method for producing polyurethane resin using same |
Non-Patent Citations (1)
| Title |
|---|
| 朱延新等: "2,2,6,6-四甲基-3,5-庚二酮的制备", 《合成化学》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107879919A (en) * | 2018-01-09 | 2018-04-06 | 台州泰捷化工科技有限公司 | A kind of preparation method of the heptadione of medicine intermediate 3,5 |
| CN108002996A (en) * | 2018-01-09 | 2018-05-08 | 台州泰捷化工科技有限公司 | A kind of preparation method of medicine intermediate beta-diketone compound |
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