CN107011301A - One kind 2（2 methoxyphenyls）The preparation method of the carboxylic acid of 5 oxo-tetrahydrofuran 3 - Google Patents
One kind 2（2 methoxyphenyls）The preparation method of the carboxylic acid of 5 oxo-tetrahydrofuran 3 Download PDFInfo
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
The invention discloses one kind 2（2 methoxyphenyls）The high-efficiency synthesis method of the carboxylic acid of 5 oxo-tetrahydrofuran 3, using o-methoxybenzaldehyde, succinic anhydride as raw material, uses caddy/triethylamine for catalyst, 2 is obtained by reaction in aprotic atent solvent（2 methoxyphenyls）The carboxylic acid of 5 oxo-tetrahydrofuran 3, synthesis technique reaction raw materials of the invention are cheap and easy to get, and course of reaction is simply easily controlled, and product post-processing step is few, high income, and product purity is high, and cost is low, adapt to large-scale industrial production.The preparation method of the present invention overcome use in the prior art zinc chloride as catalyst when must high temperature water removal to obtain the shortcomings of higher yields, caddy does not need high-temperature roasting water removal, is not in the situation for turning to expect difficulty, suitable industrialized production.
Description
Technical field
The present invention relates to the synthetic method technical field of tetrahydrofuran derivatives, specifically a kind of 2-（2- methoxybenzenes
Base）The preparation method of -5- oxo-tetrahydrofuran -3- carboxylic acids.
Background technology
2-（2- methoxyphenyls）- 5- oxo-tetrahydrofuran -3- carboxylic acids are commonly called as 2- methoxyl group paraconic acids, No. CAS：
117621-06-4.It is the 3- carboxylic acid -5- oxo-tetrahydrofuran derivatives of aryl substitution, is mainly used in medicine, pesticide intermediate
Synthesis, be antidiabetic thing Mitiglinide II key intermediate.
Patent WO2008089461 disclose it is a kind of be used for diabetes, cancer, inflammation, nerve decline illness, infection and
The synthesis of the cyclohexadione compounds of angiocardiopathy and application process.- 3- the carboxylic acids wherein replaced comprising related intermediate aryl-
The synthesis of 5- oxo-tetrahydrofurans and separation process.Wherein o-methoxybenzaldehyde and succinic anhydride is in zinc chloride/tri-
The lower room temperature reaction 24h of ethamine catalysis, obtains 2-（2- methoxyphenyls）- 5- oxo-tetrahydrofuran -3- carboxylic acids, yield only has 49%.
Patent WO2005040109 discloses a kind of black cortical hormone receptor chemical combination for being used to treat casting skin matter hormone disturbance
The structure and application method of thing.It is directed to the paraconic acid synthetic method of step important intermediate aryl substitution.In toluene solvant
In, using anhydrous sodium acetate as catalyst, 4- chlorobenzaldehydes obtain 2- with succinic anhydride back flow reaction（4- chlorphenyls）- 5- oxos four
Hydrogen furans -3- carboxylic acids, yield 33%.
The Joe A. Tran of American Psychiatry endocrine bioscience research institute（Bioorganic &Medicinal
Chemistry Letters 18（2008）1124-1130）Et al. have studied thiophane as the black acceptor of cortin -4
With the synthetic method of tetrahydrofuran derivatives.It wherein also contains 4-chloro-benzaldehyde and prepare corresponding paraconic acid to succinic anhydride reaction
The step of, its synthetic technology method is consistent with patent WO2005040109.
The important defect of the presence of above-mentioned synthetic method：1st, reaction yield is low, and highest only has 49%, and processing procedure is cumbersome, closes
It is high into cost.2nd, experimenter has found in experimentation, and zinc chloride hygroscopicity is strong, is difficult to dry water removal, wants to obtain preferable
Yield, zinc chloride needs high-temperature roasting to remove water, and the requirement to reaction environment is high, and it is difficult to turn material, is not suitable for industrialized production.
The content of the invention
To solve the above problems, it is an object of the invention to provide a kind of 2-（2- methoxyphenyls）- 5- oxo-tetrahydrofurans-
The preparation method of 3- carboxylic acids.
The present invention to achieve the above object, is achieved through the following technical solutions：
A kind of 2-（2- methoxyphenyls）The preparation method of -5- oxo-tetrahydrofuran -3- carboxylic acids, comprises the following steps：
1. o-methoxybenzaldehyde, succinic anhydride are dissolved in aprotic solvent, caddy is then added thereto, mixed
Liquid, 0 ~ 5 DEG C is reduced to by the temperature of mixed liquor, and triethylamine is added dropwise thereto at such a temperature, and completion of dropping is warming up to reaction
20 ~ 140 DEG C of temperature, reacts 6 ~ 48 hours, obtains reaction solution；
O-methoxybenzaldehyde, succinic anhydride, aprotic solvent, the molal volume ratio of caddy and triethylamine are 0.1mol：0.1
~0.2mol：100~150ml：0.2~0.25mol：0.2~0.25mol；
The aprotic solvent is dichloromethane, chloroform, carbon tetrachloride, dichloroethanes, toluene or dimethylbenzene；
2. water is added into step 1. gained reaction solution, with salt acid for adjusting pH to 2 ~ 3, point liquid, organic phase saturated sodium bicarbonate
Solution is washed, and merges aqueous phase, will merge aqueous phase salt acid for adjusting pH to 2 ~ 3, separates out yellow solid, and filtering obtains filter cake；By gained
Filter cake re crystallization from toluene, obtains 2-（2- methoxyphenyls）- 5- oxo-tetrahydrofuran -3- carboxylic acids；Step 1. gained reaction solution,
The volume ratio of water and toluene is 1：0.8~1：0.5~1.
It is preferred that, aprotic solvent is dichloromethane or dimethylbenzene.
It is preferred that, o-methoxybenzaldehyde, succinic anhydride, dimethylbenzene, the molal volume ratio of caddy and triethylamine are
0.1mol：0.15mol：120ml：0.2mol：0.2mol.
It is preferred that, reaction temperature is 20 ~ 50 DEG C.
It is preferred that, 1. gained reaction solution, the volume ratio of water and toluene are 1 to step：1：0.5.
Further preferred preparation method, comprises the following steps：
1. o-methoxybenzaldehyde, succinic anhydride are dissolved in aprotic solvent dimethylbenzene, caddy is then added thereto, obtained
To mixed liquor, the temperature of mixed liquor is reduced to 0 DEG C, and triethylamine is added dropwise thereto at such a temperature, completion of dropping is warming up to
50 DEG C of reaction temperature, reacts 15 hours, obtains reaction solution；
O-methoxybenzaldehyde, succinic anhydride, aprotic solvent dimethylbenzene, the molal volume ratio of caddy and triethylamine are
0.1mol：0.15mol：120ml：0.2mol：0.2mol；
2. water is added into step 1. gained reaction solution, with salt acid for adjusting pH to 2, point liquid, organic phase is molten with saturated sodium bicarbonate
Liquid is washed, and merges aqueous phase, will merge aqueous phase salt acid for adjusting pH to 2, separates out yellow solid, and filtering obtains filter cake；By gained filter cake
With re crystallization from toluene, 2- is obtained（2- methoxyphenyls）- 5- oxo-tetrahydrofuran -3- carboxylic acids；Step 1. gained reaction solution, water and
The volume ratio of toluene is 1：1：0.5.
The present invention has advantages below compared with prior art：
The invention provides 2-（2- methoxyphenyls）The new process route of the synthesis of -5- oxo-tetrahydrofuran -3- carboxylic acids, with
O-methoxybenzaldehyde and succinic anhydride are raw material, and using caddy/triethylamine as catalyst, reaction raw materials are cheap and easy to get, reaction
Process is simply easily controlled, and product post-processing step is few, high income, and product purity is high, and cost is low, adapts to large-scale industry metaplasia
Production.
The preparation method of the present invention overcomes to be removed water using zinc chloride as the when necessary high temperature of catalyst in the prior art
To obtain the shortcoming of higher yields, caddy does not need high-temperature roasting water removal, is not in turn the difficult situation of material, suitable industry
Metaplasia is produced.
Embodiment
It is an object of the invention to provide a kind of 2-（2- methoxyphenyls）The preparation side of -5- oxo-tetrahydrofuran -3- carboxylic acids
Method, is achieved through the following technical solutions：
The synthetic method of the present invention, using o-methoxybenzaldehyde, succinic anhydride as raw material, uses caddy/triethylamine for catalysis
Agent, target product is obtained by single step reaction, and its reaction scheme is：
。
A kind of 2-（2- methoxyphenyls）The preparation method of -5- oxo-tetrahydrofuran -3- carboxylic acids, comprises the following steps：
1. o-methoxybenzaldehyde, succinic anhydride are dissolved in aprotic solvent, caddy is then added thereto, mixed
Liquid, 0 ~ 5 DEG C is reduced to by the temperature of mixed liquor, and triethylamine is added dropwise thereto at such a temperature, and completion of dropping is warming up to reaction
20 ~ 140 DEG C of temperature, reacts 6 ~ 48 hours, obtains reaction solution；
O-methoxybenzaldehyde, succinic anhydride, aprotic solvent, the molal volume ratio of caddy and triethylamine are 0.1mol：0.1
~0.2mol：100~150ml：0.2~0.25mol：0.2~0.25mol；
The aprotic solvent is dichloromethane, chloroform, carbon tetrachloride, dichloroethanes, toluene or dimethylbenzene；
2. water is added into step 1. gained reaction solution, with salt acid for adjusting pH to 2 ~ 3, point liquid, organic phase saturated sodium bicarbonate
Solution is washed, and merges aqueous phase, will merge aqueous phase salt acid for adjusting pH to 2 ~ 3, separates out yellow solid, and filtering obtains filter cake；By gained
Filter cake re crystallization from toluene, obtains 2-（2- methoxyphenyls）- 5- oxo-tetrahydrofuran -3- carboxylic acids；Step 1. gained reaction solution,
The volume ratio of water and toluene is 1：0.8~1：0.5~1.
It is preferred that, aprotic solvent is dichloromethane or dimethylbenzene.
It is preferred that, o-methoxybenzaldehyde, succinic anhydride, dimethylbenzene, the molal volume ratio of caddy and triethylamine are
0.1mol：0.15mol：120ml：0.2mol：0.2mol.
It is preferred that, reaction temperature is 20 ~ 50 DEG C.
It is preferred that, 1. gained reaction solution, the volume ratio of water and toluene are 1 to step：1：0.5.
Further preferred preparation method, comprises the following steps：
1. o-methoxybenzaldehyde, succinic anhydride are dissolved in aprotic solvent dimethylbenzene, caddy is then added thereto, obtained
To mixed liquor, the temperature of mixed liquor is reduced to 0 DEG C, and triethylamine is added dropwise thereto at such a temperature, completion of dropping is warming up to
50 DEG C of reaction temperature, reacts 15 hours, obtains reaction solution；
O-methoxybenzaldehyde, succinic anhydride, aprotic solvent dimethylbenzene, the molal volume ratio of caddy and triethylamine are
0.1mol：0.15mol：120ml：0.2mol：0.2mol；
2. water is added into step 1. gained reaction solution, with salt acid for adjusting pH to 2, point liquid, organic phase is molten with saturated sodium bicarbonate
Liquid is washed, and merges aqueous phase, will merge aqueous phase salt acid for adjusting pH to 2, separates out yellow solid, and filtering obtains filter cake；By gained filter cake
With re crystallization from toluene, 2- is obtained（2- methoxyphenyls）- 5- oxo-tetrahydrofuran -3- carboxylic acids；Step 1. gained reaction solution, water and
The volume ratio of toluene is 1：1：0.5.
Below in conjunction with specific embodiment, the invention will be further described.
Embodiment 1
A kind of 2-（2- methoxyphenyls）The preparation method of -5- oxo-tetrahydrofuran -3- carboxylic acids, comprises the following steps：
1. 13.6g o-methoxybenzaldehydes, 10g succinic anhydrides are dissolved in 100ml dichloromethane, then added thereto
36.6g caddies, obtain mixed liquor, and the temperature of mixed liquor is reduced into 0 DEG C, and 20.2g tri- is added dropwise thereto at such a temperature
Ethamine, completion of dropping is warming up to 20 DEG C of reaction temperature, reacts 48 hours, obtains reaction solution；
2. the water of 0.8 times of reaction solution volume, with salt acid for adjusting pH to 2, point liquid, organic phase are added into step 1. gained reaction solution
Washed with saturated sodium bicarbonate solution, merge aqueous phase, aqueous phase salt acid for adjusting pH to 2 will be merged, yellow solid is separated out, filtered,
Obtain filter cake；By re crystallization from toluene of the gained filter cake with 0.5 times of reaction solution volume, 21.54g 2- are obtained（2- methoxyphenyls）-5-
Oxo-tetrahydrofuran -3- carboxylic acids, product is faint yellow solid, and yield is 91.2%, is 98.6% with HPLC detection purity.
Embodiment 2
A kind of 2-（2- methoxyphenyls）The preparation method of -5- oxo-tetrahydrofuran -3- carboxylic acids, comprises the following steps：
1. 13.6g o-methoxybenzaldehydes, 20g succinic anhydrides are dissolved in 150ml chloroforms, 45.75g chlorine is then added thereto
Cadmium, obtains mixed liquor, and the temperature of mixed liquor is reduced into 5 DEG C, and 25.25g triethylamines, drop is added dropwise thereto at such a temperature
Add to finish and be warming up to 140 DEG C of reaction temperature, react 6 hours, obtain reaction solution；
2. isometric water is added into step 1. gained reaction solution, with salt acid for adjusting pH to 3, point liquid, organic phase saturated carbon
Sour hydrogen sodium solution washing, merges aqueous phase, will merge aqueous phase salt acid for adjusting pH to 3, separates out yellow solid, and filtering obtains filter cake；Will
Gained filter cake is used and the isometric re crystallization from toluene of water, obtains 21.68g 2-（2- methoxyphenyls）- 5- oxo-tetrahydrofurans-
3- carboxylic acids, product is faint yellow solid, and yield is 91.8%, is 99.0% with HPLC detection purity.
Embodiment 3
A kind of 2-（2- methoxyphenyls）The preparation method of -5- oxo-tetrahydrofuran -3- carboxylic acids, comprises the following steps：
1. 13.6g o-methoxybenzaldehydes, 12g succinic anhydrides are dissolved in 140ml carbon tetrachloride, then added thereto
43.92g caddies, obtain mixed liquor, and the temperature of mixed liquor is reduced into 4 DEG C, and 22.22g is added dropwise thereto at such a temperature
Triethylamine, completion of dropping is warming up to 100 DEG C of reaction temperature, reacts 20 hours, obtains reaction solution；
2. the water of 0.9 times of reaction solution volume, with salt acid for adjusting pH to 3, point liquid, organic phase are added into step 1. gained reaction solution
Washed with saturated sodium bicarbonate solution, merge aqueous phase, aqueous phase salt acid for adjusting pH to 3 will be merged, yellow solid is separated out, filtered,
Obtain filter cake；By re crystallization from toluene of the gained filter cake with 0.6 times of reaction solution volume, 21.83g 2- are obtained（2- methoxyphenyls）-5-
Oxo-tetrahydrofuran -3- carboxylic acids, product is faint yellow solid, and yield is 92.4%, is 99.0% with HPLC detection purity.
Embodiment 4
A kind of 2-（2- methoxyphenyls）The preparation method of -5- oxo-tetrahydrofuran -3- carboxylic acids, comprises the following steps：
1. 13.6g o-methoxybenzaldehydes, 15g succinic anhydrides are dissolved in 120ml dimethylbenzene, 36.6g is then added thereto
Caddy, obtains mixed liquor, and the temperature of mixed liquor is reduced into 0 DEG C, and is added dropwise 20.2g triethylamines thereto at such a temperature,
Completion of dropping is warming up to 50 DEG C of reaction temperature, reacts 15 hours, obtains reaction solution；
2. isometric water is added into step 1. gained reaction solution, with salt acid for adjusting pH to 2, point liquid, organic phase saturated carbon
Sour hydrogen sodium solution washing, merges aqueous phase, will merge aqueous phase salt acid for adjusting pH to 2, separates out yellow solid, and filtering obtains filter cake；Will
The gained filter cake re crystallization from toluene of 0.5 times of reaction solution volume, obtains 22.16g2-（2- methoxyphenyls）- 5- oxo tetrahydrochysene furans
Mutter -3- carboxylic acids, product is faint yellow solid, and yield is 93.8%, be 99.5% with HPLC detection purity.
Comparative example 1
13.6g is put into 1L four-hole boiling flasks（0.1mol）O-methoxybenzaldehyde, 30.4g（0.3mol）Succinic anhydride, 61.6g
（0.44mol）Anhydrous zinc chloride（It is commercially available）With 360g dichloromethane, 40.8g is added dropwise at 0 DEG C（0.4mol）Triethylamine, keeps being added dropwise
0-5 DEG C of temperature.Back flow reaction 24h is heated to after dripping off, 250mL water is poured into, pH=3 is acidified to concentrated hydrochloric acid.Divide liquid, water layer is used
Dichloromethane is extracted twice, and is merged oil reservoir, is used 100mL water washings.Obtained dichloromethane layer uses saturated sodium bicarbonate solution again
Washing 3 times.Water layer is added dropwise concentrated hydrochloric acid and is acidified to pH=3, separates out solid.Add 200g dichloromethane, stirring and dissolving, point liquid.Oil reservoir
Removed under reduced pressure solvent, residue 80g re crystallization from toluene obtains faint yellow solid product 7.0g, content 81.4%, yield 29%.
Comparative example 2
13.6g is put into 1L four-hole boiling flasks（0.1mol）O-methoxybenzaldehyde, 25.3g（0.25mol）Succinic anhydride,
61.6g（0.44mol）Anhydrous zinc chloride（Handled by high-temperature roasting）With 360g dichloromethane, 20.4g is added dropwise at 0 DEG C
（0.2mol）Triethylamine, keeps 0-5 DEG C of dropping temperature.44 DEG C of back flow reaction 24h are heated to after dripping off, 250mL water is poured into, with dense
Hydrochloric acid is acidified to pH=2.Divide liquid, water layer is extracted twice with dichloromethane, merge oil reservoir, use 100mL water washings.Obtained dichloro
Methane layer is washed 3 times with saturated sodium bicarbonate solution again.Water layer is added dropwise concentrated hydrochloric acid and is acidified to pH=2, separates out solid.Add 200g
Dichloromethane, stirring and dissolving, point liquid.Oil reservoir removed under reduced pressure solvent, residue 80g re crystallization from toluene, obtains faint yellow solid
Product 15.8g, content 80.6%, yield 66.7%.
Claims (7)
1. a kind of 2-（2- methoxyphenyls）The preparation method of -5- oxo-tetrahydrofuran -3- carboxylic acids, it is characterised in that：Including with
Lower step：
1. o-methoxybenzaldehyde, succinic anhydride are dissolved in aprotic solvent, caddy is then added thereto, mixed
Liquid, 0 ~ 5 DEG C is reduced to by the temperature of mixed liquor, and triethylamine is added dropwise thereto at such a temperature, and completion of dropping is warming up to reaction
20 ~ 140 DEG C of temperature, reacts 6 ~ 48 hours, obtains reaction solution；
O-methoxybenzaldehyde, succinic anhydride, aprotic solvent, the molal volume ratio of caddy and triethylamine are 0.1mol：0.1
~0.2mol：100~150ml：0.2~0.25mol：0.2~0.25mol；
The aprotic solvent is dichloromethane, chloroform, carbon tetrachloride, dichloroethanes, toluene or dimethylbenzene；
2. water is added into step 1. gained reaction solution, with salt acid for adjusting pH to 2 ~ 3, point liquid, organic phase saturated sodium bicarbonate
Solution is washed, and merges aqueous phase, will merge aqueous phase salt acid for adjusting pH to 2 ~ 3, separates out yellow solid, and filtering obtains filter cake；By gained
Filter cake re crystallization from toluene, obtains 2-（2- methoxyphenyls）- 5- oxo-tetrahydrofuran -3- carboxylic acids；Step 1. gained reaction solution,
The volume ratio of water and toluene is 1：0.8~1：0.5~1.
2. 2- according to claim 1（2- methoxyphenyls）The preparation method of -5- oxo-tetrahydrofuran -3- carboxylic acids, its
It is characterised by：The aprotic solvent is dichloromethane or dimethylbenzene.
3. 2- according to claim 1（2- methoxyphenyls）The preparation method of -5- oxo-tetrahydrofuran -3- carboxylic acids, its
It is characterised by：O-methoxybenzaldehyde, succinic anhydride, dimethylbenzene, the molal volume ratio of caddy and triethylamine are 0.1mol：
0.15mol：120ml：0.2mol：0.2mol.
4. 2- according to claim 1（2- methoxyphenyls）The preparation method of -5- oxo-tetrahydrofuran -3- carboxylic acids, its
It is characterised by：Reaction temperature is 20 ~ 50 DEG C.
5. 2- according to claim 1（2- methoxyphenyls）The preparation method of -5- oxo-tetrahydrofuran -3- carboxylic acids, its
It is characterised by：Reaction time is 12 ~ 15 hours.
6. 2- according to claim 1（2- methoxyphenyls）The preparation method of -5- oxo-tetrahydrofuran -3- carboxylic acids, its
It is characterised by：1. gained reaction solution, the volume ratio of water and toluene are 1 to step：1：0.5.
7. 2- according to claim 1（2- methoxyphenyls）The preparation method of -5- oxo-tetrahydrofuran -3- carboxylic acids, its
It is characterised by：Comprise the following steps：
1. o-methoxybenzaldehyde, succinic anhydride are dissolved in aprotic solvent dimethylbenzene, caddy is then added thereto, obtained
To mixed liquor, the temperature of mixed liquor is reduced to 0 DEG C, and triethylamine is added dropwise thereto at such a temperature, completion of dropping is warming up to
50 DEG C of reaction temperature, reacts 15 hours, obtains reaction solution；
O-methoxybenzaldehyde, succinic anhydride, aprotic solvent dimethylbenzene, the molal volume ratio of caddy and triethylamine are
0.1mol：0.15mol：120ml：0.2mol：0.2mol；
2. water is added into step 1. gained reaction solution, with salt acid for adjusting pH to 2, point liquid, organic phase is molten with saturated sodium bicarbonate
Liquid is washed, and merges aqueous phase, will merge aqueous phase salt acid for adjusting pH to 2, separates out yellow solid, and filtering obtains filter cake；By gained filter cake
With re crystallization from toluene, 2- is obtained（2- methoxyphenyls）- 5- oxo-tetrahydrofuran -3- carboxylic acids；Step 1. gained reaction solution, water
Volume ratio with toluene is 1：1：0.5.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005040109A1 (en) * | 2003-10-22 | 2005-05-06 | Neurocrine Biosciences, Inc. | Ligands of melanocortin receptors and compositions and methods related thereto |
| WO2010124005A1 (en) * | 2009-04-21 | 2010-10-28 | Purdue Research Foundation | Octahydrobenzoisoquinoline modulators of dopamine receptors and uses therefor |
| CN106554334A (en) * | 2015-09-30 | 2017-04-05 | 山东省联合农药工业有限公司 | A kind of nematicide containing lactonic ring and its production and use |
-
2017
- 2017-05-27 CN CN201710388412.0A patent/CN107011301B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005040109A1 (en) * | 2003-10-22 | 2005-05-06 | Neurocrine Biosciences, Inc. | Ligands of melanocortin receptors and compositions and methods related thereto |
| WO2010124005A1 (en) * | 2009-04-21 | 2010-10-28 | Purdue Research Foundation | Octahydrobenzoisoquinoline modulators of dopamine receptors and uses therefor |
| CN106554334A (en) * | 2015-09-30 | 2017-04-05 | 山东省联合农药工业有限公司 | A kind of nematicide containing lactonic ring and its production and use |
Non-Patent Citations (1)
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| 鲁正熹等: "芳基取代的3-羧酸-5-氧代-四氢呋喃衍生物的合成", 《化工中间体》 * |
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