CN109678825A - A kind of synthetic method of Methoxvbenzofuran ketone - Google Patents
A kind of synthetic method of Methoxvbenzofuran ketone Download PDFInfo
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- CN109678825A CN109678825A CN201910069832.1A CN201910069832A CN109678825A CN 109678825 A CN109678825 A CN 109678825A CN 201910069832 A CN201910069832 A CN 201910069832A CN 109678825 A CN109678825 A CN 109678825A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
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Abstract
The invention discloses a kind of synthetic methods of Methoxvbenzofuran ketone, and steps are as follows: o-chlorobenzene acetic acid, liquid alkaline, catalyst 1 being reacted, distillation dehydration after being acidified with concentrated hydrochloric acid, cyclization after dehydration, then alkali cleaning, washing, concentration;The benzofuranone of trimethyl orthoformate and acetic anhydride and synthesis is reacted, reaction terminates depickling, dissolution, washing, precipitation, obtains Methoxvbenzofuran ketone;The present invention first synthesizes benzofuranone from o-chlorobenzene acetic acid, by benzofuranone and trimethyl orthoformate, the further synthesizing methoxy benzofuranone of acetic anhydride, it is persistently acidified, is dehydrated in reaction process, alkali cleaning, washing, distillation, the benzofuranone of initial synthesis is not only purified, improve the purity of benzofuranone, and improve the purity of Methoxvbenzofuran ketone, wherein, it is detected by high performance liquid chromatography, the purity of Methoxvbenzofuran ketone is up to 98% or more, and yield 90% can reach above.
Description
Technical field
The present invention relates to organic chemical synthesis technical fields, and in particular to a kind of synthesis side of Methoxvbenzofuran ketone
Method.
Background technique
Fluoxastrobin is the methoxy acrylate fungicide or strobilurins analog developed by Syngenta Co., Ltd.It is phonetic
Bacterium ester can be used for cereal, rice, grape, potato, vegetables, fruit tree and other stem of plant foliar spray mists, seed treatment, can also be into
Row soil treatment.Fluoxastrobin under recommended dose use to crop safety, without phytotoxicity, to underground water, Environmental security.It has height
Effect, wide spectrum, protection, treat, root out, permeating, systemic activity the features such as, to nearly all Mycophytes germ evil have good work
Property.Fluoxastrobin is that another class of pesticide circle after triazole bactericidal agent is killed with the novel agricultural of the market vitality with development potential
Microbial inoculum.Since the producer of domestic production this product is less, Fluoxastrobin has very big market at home, has hair well
Open up future.
3- (a- methoxyl group) methene benzofuran -2 (3H) -one is synthesizing methoxy acrylic bactericide Fluoxastrobin
Important intermediate, 3- (a- methoxyl group) methene benzofuran -2 (3H) -one synthetic reaction low yield in the prior art, produce
Object purity is not also high, causes 3- (a- methoxyl group) (3H) -one of methene benzofuran -2 in the subsequent synthetic run of Fluoxastrobin
Other impurities are introduced, the reduction of final product yield is directly resulted in, purity reduces.
Summary of the invention
To solve the above problems, the present invention is directed to the bases of existing 3- (a- methoxyl group) methene benzofuran -2 (3H) -one
On plinth, under the premise of not increasing chemical contamination, to 3- (a- methoxyl group) methene benzofuran -2 (3H) -one synthesis technology
Part operation optimizes, and is produced with improving the synthesis of 3- (a- methoxyl group) methene benzofuran -2 (3H) -one and Fluoxastrobin
Rate and purity.
Purpose to realize the present invention, the technical solution adopted is that: a kind of synthetic method of Methoxvbenzofuran ketone, it is described
Specific step is as follows for synthesis technology:
1) is hydroxylated: by the o-chlorobenzene acetic acid measured, liquid alkaline, the investment of catalyst 1 to autoclave, nitrogen is opened in starting stirring
Gas pressurization after be warming up to 140~145 DEG C of reactions, after transfer the material into acidolysis kettle;
2) is acidified: material being cooled to 25 DEG C hereinafter, under stirring, slowly stream adds into acidolysis kettle with concentrated hydrochloric acid, adjusts
PH value is saved, during adjusting pH value, control temperature is lower than 22 DEG C;
3) is dehydrated: the toluene measured being put into dehydrating kettle, is warming up to 90~110 DEG C, azeotropic distillation dehydration is dehydrated
After material go in cyclization kettle;
4) cyclization: the concentrated sulfuric acid measured being put into cyclization kettle and dehydrated material stirs together, with collet recirculated water
Temperature in the kettle is controlled at 60~70 DEG C;
5) alkali cleaning: material is put to alkali cleaning kettle after cyclization, the base reagent measured, alkali cleaning temperature is added in starting stirring
At 40~50 DEG C, organic materials is transferred to washing kettle after alkali cleaning by stratification for degree control;
6) is washed: the water measured being put to washing kettle and material and is stirred together, temperature is controlled at 40~50 DEG C, is stood
After layering, the upper layer bed of material is transferred to concentration kettle;
7) distills: opening the vacuum system of concentration kettle, slowly heats up under vacuum state, starts piptonychia benzene, when kettle temperature rises to
80 DEG C, when toluene is without extraction, benzofuranone pan tank is switched to, starts to collect benzofuranone, until terminating, distillation still residue
It is handled after staying collection as dangerous waste;
8) is synthesized: the benzofuranone that the trimethyl orthoformate measured and acetic anhydride and step 7 synthesize successively is thrown
Enter into synthesis reactor, be to slowly warm up to 90 DEG C, starts to receive methyl acetate, and do not surpassed with the reflux ratio of tower control synthesis reactor temperature
100 DEG C are crossed, when tower temperature increases, and methyl acetate is without extraction, reaction terminates, and after material is cooled to 80 DEG C, is transferred to depickling kettle;
9) depickling: depickling kettle is first vacuumized, and controls temperature of charge at 80 DEG C, starts de- acetic acid, by object after depickling
Material is cooled to 40 DEG C, is transferred to dissolution kettle;
10) is extracted: the toluene measured being put into dissolution kettle and after material is sufficiently stirred, organic layer material is transferred to
Washing kettle, water layer material carry out waste disposal;
11) is washed: the water measured being put to washing kettle and material to be sufficiently stirred is warming up to 40~50 DEG C, stand point
Layer washes off wherein remaining acid and impurity, organic layer and is transferred to precipitation kettle;
12) precipitation: open precipitation kettle vacuum system, by precipitation kettle temperature of charge control at 80 DEG C, start piptonychia benzene and
The azeotropic mixture of water, after piptonychia benzene, control Methoxvbenzofuran ketone concentration, terminate precipitation, cool down simultaneously material is shifted
To the measuring tank of Methoxvbenzofuran ketone.
Further, the concentration of liquid alkaline is 30~40% in the synthetic method step 1.
Further, nitrogen moulding pressure is 0.4~0.45MPa in the synthetic method step 1.
Further, concentrated hydrochloric acid adjusts pH value to 6.5~7.0 in the synthetic method step 2.
Further, base reagent is one in sodium bicarbonate, sodium hydroxide or sodium bicarbonate in the synthetic method step 5
Kind is several.
Further, in the synthetic method step 7 vacuum system by vacuum control more than -0.09MPa.
Further, vacuum is evacuated to -0.09MPa or more in the synthetic method step 9.
Further, in the synthetic method step 12 vacuum system by vacuum control more than -0.097MPa.
Further, Methoxvbenzofuran ketone concentration control when terminating precipitation in the synthetic method step 12 exists
55%.
The invention has the benefit that the present invention first synthesizes benzofuranone from o-chlorobenzene acetic acid, by benzo furan
It mutters ketone and trimethyl orthoformate, the further synthesizing methoxy benzofuranone of acetic anhydride, is persistently acidified, is taken off in reaction process
Water, alkali cleaning, washing, distillation, have not only purified the benzofuranone of initial synthesis, improve the pure of benzofuranone
Degree, and improve the purity of Methoxvbenzofuran ketone, wherein it is detected by high performance liquid chromatography, methoxyl group benzo furan
The purity of ketone of muttering is up to 98% or more, and yield 90% reaches above, reaction waste collect handles, and avoids toxic
Material enters directly into environment, causes environmental pollution.
Specific embodiment
Below in conjunction with the embodiment of the present invention, technical solution of the present invention is clearly and completely described, it is clear that
Described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.Based on the implementation in the present invention
Example, every other embodiment obtained by those of ordinary skill in the art without making creative efforts belong to
The scope of protection of the invention.
Embodiment 1
By the o-chlorobenzene acetic acid measured, 40% liquid alkaline, the investment of catalyst 1 to autoclave, starting stirring is opened nitrogen and is added
Be warming up to 145 DEG C of reactions after being depressed into 0.45MPa, after transfer the material into acidolysis kettle;Material is cooled to 25 DEG C hereinafter, stirring
It mixes under state, with concentrated hydrochloric acid, into acidolysis kettle, slowly stream adds, and adjusts pH value to 7.0, during adjusting pH value, control temperature is low
In 22 DEG C;The toluene measured is put into dehydrating kettle, is warming up to 110 DEG C, azeotropic distillation dehydration, material is gone to after dehydration
In cyclization kettle;The concentrated sulfuric acid measured is put into cyclization kettle and dehydrated material stirs together, in collet circulation water management kettle
Temperature is at 70 DEG C;Material is put to alkali cleaning kettle after cyclization, the sodium bicarbonate measured, sodium hydroxide is added in starting stirring
Or sodium bicarbonate solution, alkali cleaning temperature are controlled at 50 DEG C, organic materials is transferred to washing kettle after alkali cleaning by stratification;
The water measured to be put to washing kettle and material and is stirred together, temperature is controlled at 50 DEG C, after stratification, the transfer of the upper layer bed of material
To concentration kettle;The vacuum system of concentration kettle is opened, vacuum system more than -0.095MPa, delays vacuum control under vacuum state
Slow heating, starts piptonychia benzene, when kettle temperature rises to 80 DEG C, when toluene is without extraction, switches to benzofuranone pan tank, starts to collect
Benzofuranone, until terminating, distillation still residual is handled after collecting as dangerous waste;By the trimethyl orthoformate measured and acetic acid
Acid anhydride and the benzofuranone of synthesis are successively put into synthesis reactor, are to slowly warm up to 90 DEG C, are started to receive methyl acetate, are used in combination
The reflux ratio control synthesis reactor temperature of tower is no more than 100 DEG C, and when tower temperature increases, and methyl acetate is without extraction, reaction terminates, by object
After material is cooled to 80 DEG C, it is transferred to depickling kettle;Depickling kettle is first vacuumized, vacuum is evacuated to -0.095MPa or more, controls material temperature
Degree starts de- acetic acid, material is cooled to 40 DEG C after depickling, is transferred to dissolution kettle at 80 DEG C;The toluene measured is put
Enter dissolution kettle and after material is sufficiently stirred, organic layer material is transferred to washing kettle, water layer material carries out waste disposal;It will meter
Measured water, which is put to washing kettle and material to be sufficiently stirred, is warming up to 50 DEG C, and stratification washes off wherein remaining acid and impurity,
Organic layer is transferred to precipitation kettle;The vacuum system of precipitation kettle is opened, vacuum control is more than -0.097MPa, by precipitation kettle material
Temperature control at 80 DEG C, start piptonychia benzene and water azeotropic mixture, after piptonychia benzene, control Methoxvbenzofuran ketone concentration
It is 55%, terminates precipitation, cool down and transfer the material into the measuring tank of Methoxvbenzofuran ketone;HPLC tests and analyzes 3- (a-
Methoxyl group) methene benzofuran -2 (3H) -one purity be 98.7%, yield 95.3%.
Embodiment 2
By the o-chlorobenzene acetic acid measured, 30% liquid alkaline, the investment of catalyst 1 to autoclave, starting stirring is opened nitrogen and is added
Be warming up to 140 DEG C of reactions after being depressed into 0.4MPa, after transfer the material into acidolysis kettle;Material is cooled to 25 DEG C hereinafter, stirring
It mixes under state, with concentrated hydrochloric acid, into acidolysis kettle, slowly stream adds, and adjusts pH value to 6.5, during adjusting pH value, control temperature is low
In 22 DEG C;The toluene measured is put into dehydrating kettle, is warming up to 90 DEG C, azeotropic distillation dehydration, material is gone to after dehydration
In cyclization kettle;The concentrated sulfuric acid measured is put into cyclization kettle and dehydrated material stirs together, in collet circulation water management kettle
Temperature is at 60 DEG C;Material is put to alkali cleaning kettle after cyclization, the sodium bicarbonate measured, sodium hydroxide is added in starting stirring
Or sodium bicarbonate solution, alkali cleaning temperature are controlled at 40 DEG C, organic materials is transferred to washing kettle after alkali cleaning by stratification;
The water measured to be put to washing kettle and material and is stirred together, temperature is controlled at 40 DEG C, after stratification, the transfer of the upper layer bed of material
To concentration kettle;Open concentration kettle vacuum system, vacuum system by vacuum control more than -0.1MPa, under vacuum state slowly
Heating starts piptonychia benzene, when kettle temperature rises to 80 DEG C, and toluene is without extraction, switches to benzofuranone pan tank, starts to collect benzene
And furanone, until terminating, distillation still residual is handled after collecting as dangerous waste;By the trimethyl orthoformate measured and acetic anhydride
And the benzofuranone of synthesis is successively put into synthesis reactor, is to slowly warm up to 90 DEG C, starts to receive methyl acetate, and use tower
Reflux ratio control synthesis reactor temperature be no more than 100 DEG C, when tower temperature increase, methyl acetate without extraction when, reaction terminates, by material
After being cooled to 80 DEG C, it is transferred to depickling kettle;Depickling kettle is first vacuumized, vacuum is evacuated to -0.1MPa or more, and control temperature of charge exists
80 DEG C, starts de- acetic acid, material is cooled to 40 DEG C after depickling, is transferred to dissolution kettle;The toluene measured is put into molten
After solution kettle and material are sufficiently stirred, organic layer material is transferred to washing kettle, water layer material carries out waste disposal;It will measure
Water put to washing kettle and material to be sufficiently stirred and be warming up to 40 DEG C, stratification washes off wherein remaining acid and impurity, organic
Layer is transferred to precipitation kettle;The vacuum system of precipitation kettle is opened, vacuum control is more than -0.1MPa, by precipitation kettle temperature of charge control
System at 80 DEG C, start piptonychia benzene and water azeotropic mixture, after piptonychia benzene, control Methoxvbenzofuran ketone concentration be
55%, terminate precipitation, cools down and transfer the material into the measuring tank of Methoxvbenzofuran ketone;HPLC tests and analyzes 3- (a- first
Oxygroup) methene benzofuran -2 (3H) -one purity 98.1%, yield 93.7%.
Embodiment 3
By the o-chlorobenzene acetic acid measured, 32% liquid alkaline, the investment of catalyst 1 to autoclave, starting stirring is opened nitrogen and is added
Be warming up to 145 DEG C of reactions after being depressed into 0.45MPa, after transfer the material into acidolysis kettle;Material is cooled to 25 DEG C hereinafter, stirring
It mixes under state, with concentrated hydrochloric acid, into acidolysis kettle, slowly stream adds, and adjusts pH value to 6.5, during adjusting pH value, control temperature is low
In 22 DEG C;The toluene measured is put into dehydrating kettle, is warming up to 110 DEG C, azeotropic distillation dehydration, material is gone to after dehydration
In cyclization kettle;The concentrated sulfuric acid measured is put into cyclization kettle and dehydrated material stirs together, in collet circulation water management kettle
Temperature is at 70 DEG C;Material is put to alkali cleaning kettle after cyclization, the sodium bicarbonate measured, sodium hydroxide is added in starting stirring
Or sodium bicarbonate solution, alkali cleaning temperature are controlled at 50 DEG C, organic materials is transferred to washing kettle after alkali cleaning by stratification;
The water measured to be put to washing kettle and material and is stirred together, temperature is controlled at 50 DEG C, after stratification, the transfer of the upper layer bed of material
To concentration kettle;Open concentration kettle vacuum system, vacuum system by vacuum control more than -0.1MPa, under vacuum state slowly
Heating starts piptonychia benzene, when kettle temperature rises to 80 DEG C, and toluene is without extraction, switches to benzofuranone pan tank, starts to collect benzene
And furanone, until terminating, distillation still residual is handled after collecting as dangerous waste;By the trimethyl orthoformate measured and acetic anhydride
And the benzofuranone of synthesis is successively put into synthesis reactor, is to slowly warm up to 90 DEG C, starts to receive methyl acetate, and use tower
Reflux ratio control synthesis reactor temperature be no more than 100 DEG C, when tower temperature increase, methyl acetate without extraction when, reaction terminates, by material
After being cooled to 80 DEG C, it is transferred to depickling kettle;Depickling kettle is first vacuumized, vacuum is evacuated to -0.1MPa or more, and control temperature of charge exists
80 DEG C, starts de- acetic acid, material is cooled to 40 DEG C after depickling, is transferred to dissolution kettle;The toluene measured is put into molten
After solution kettle and material are sufficiently stirred, organic layer material is transferred to washing kettle, water layer material carries out waste disposal;It will measure
Water put to washing kettle and material to be sufficiently stirred and be warming up to 50 DEG C, stratification washes off wherein remaining acid and impurity, organic
Layer is transferred to precipitation kettle;The vacuum system of precipitation kettle is opened, vacuum control is more than -0.097MPa, by precipitation kettle temperature of charge
Control at 80 DEG C, start piptonychia benzene and water azeotropic mixture, after piptonychia benzene, control Methoxvbenzofuran ketone concentration be
55%, terminate precipitation, cools down and transfer the material into the measuring tank of Methoxvbenzofuran ketone;HPLC tests and analyzes 3- (a- first
Oxygroup) methene benzofuran -2 (3H) -one purity be 99.2%, yield 96.8%.
The present invention first synthesizes benzofuranone from o-chlorobenzene acetic acid, by benzofuranone and trimethyl orthoformate,
Acetic anhydride further synthesizing methoxy benzofuranone is persistently acidified in reaction process, is dehydrated, alkali cleaning, washing, distillation etc.
Step has not only purified the benzofuranone of initial synthesis, improves the purity of benzofuranone, and improves methoxybenzene
And the purity of furanone, wherein by high performance liquid chromatography detect, the purity of Methoxvbenzofuran ketone be up to 98% with
On, yield 90% reaches above, and reaction waste has been carried out collection and has been handled, toxic material is avoided to enter directly into environment
In, environmental pollution is caused, good in economic efficiency, practicability and generalization are strong.
It although an embodiment of the present invention has been shown and described, for the ordinary skill in the art, can be with
A variety of variations, modification, replacement can be carried out to these embodiments without departing from the principles and spirit of the present invention by understanding
And modification, the scope of the present invention is defined by the appended.
Claims (9)
1. a kind of synthetic method of Methoxvbenzofuran ketone, it is characterised in that: specific step is as follows for the synthesis technology:
1) is hydroxylated: by the o-chlorobenzene acetic acid measured, liquid alkaline, the investment of catalyst 1 to autoclave, starting stirring is opened nitrogen and is added
140~145 DEG C of reactions are warming up to after pressure, after transfer the material into acidolysis kettle;
2) is acidified: material being cooled to 25 DEG C hereinafter, under stirring, slowly stream adds into acidolysis kettle with concentrated hydrochloric acid, adjusts PH
Value, during adjusting pH value, control temperature is lower than 22 DEG C;
3) is dehydrated: the toluene measured being put into dehydrating kettle, is warming up to 90~110 DEG C, azeotropic distillation dehydration, dehydration finishes
Material is gone in cyclization kettle afterwards;
4) cyclization: the concentrated sulfuric acid measured being put into cyclization kettle and dehydrated material stirs together, recycles water management with collet
Temperature in the kettle is at 60~70 DEG C;
5) alkali cleaning: material is put to alkali cleaning kettle after cyclization, the base reagent measured, alkali cleaning temperature control is added in starting stirring
For system at 40~50 DEG C, organic materials is transferred to washing kettle after alkali cleaning by stratification;
6) is washed: the water measured being put to washing kettle and material and is stirred together, temperature control is at 40~50 DEG C, stratification
Afterwards, the upper layer bed of material is transferred to concentration kettle;
7) distills: opening the vacuum system of concentration kettle, slowly heats up under vacuum state, starts piptonychia benzene, when kettle temperature rises to 80
DEG C, when toluene is without extraction, benzofuranone pan tank is switched to, starts to collect benzofuranone, until terminating, distillation still residual
It is handled after collection as dangerous waste;
8) synthesize: by the benzofuranone that the trimethyl orthoformate measured and acetic anhydride and step 7 synthesize successively put into
In synthesis reactor, 90 DEG C are to slowly warm up to, starts to receive methyl acetate, and be no more than with the reflux ratio of tower control synthesis reactor temperature
100 DEG C, when tower temperature increases, and methyl acetate is without extraction, reaction terminates, and after material is cooled to 80 DEG C, is transferred to depickling kettle;
9) depickling: depickling kettle is first vacuumized, and controls temperature of charge at 80 DEG C, is started de- acetic acid, is dropped material after depickling
Temperature is transferred to dissolution kettle to 40 DEG C;
10) is extracted: the toluene measured being put into dissolution kettle and after material is sufficiently stirred, organic layer material is transferred to washing
Kettle, water layer material carry out waste disposal;
11) is washed: the water measured being put to washing kettle and material to be sufficiently stirred is warming up to 40~50 DEG C, stratification is washed
Fall wherein remaining acid and impurity, organic layer and is transferred to precipitation kettle;
12) precipitation: opening the vacuum system of precipitation kettle, and precipitation kettle temperature of charge is controlled at 80 DEG C, piptonychia benzene and water are started
Azeotropic mixture, after piptonychia benzene, control Methoxvbenzofuran ketone concentration, terminate precipitation, cool down and transfer the material into first
The measuring tank of oxygroup benzofuranone.
2. a kind of synthetic method of Methoxvbenzofuran ketone according to claim 1, it is characterised in that: the synthesis side
The concentration of liquid alkaline is 30~40% in method step 1.
3. a kind of synthetic method of Methoxvbenzofuran ketone according to claim 1, it is characterised in that: the synthesis side
Nitrogen moulding pressure is 0.4~0.45MPa in method step 1.
4. a kind of synthetic method of Methoxvbenzofuran ketone according to claim 1, it is characterised in that: the synthesis side
Concentrated hydrochloric acid adjusts pH value to 6.5~7.0 in method step 2.
5. a kind of synthetic method of Methoxvbenzofuran ketone according to claim 1, it is characterised in that: the synthesis side
Base reagent is one or more of sodium bicarbonate, sodium hydroxide or sodium bicarbonate in method step 5.
6. a kind of synthetic method of Methoxvbenzofuran ketone according to claim 1, it is characterised in that: the synthesis side
Vacuum system is by vacuum control more than -0.09MPa in method step 7.
7. a kind of synthetic method of Methoxvbenzofuran ketone according to claim 1, it is characterised in that: the synthesis side
Vacuum is evacuated to -0.09MPa or more in method step 9.
8. a kind of synthetic method of Methoxvbenzofuran ketone according to claim 1, it is characterised in that: the synthesis side
Vacuum system is by vacuum control more than -0.097MPa in method step 12.
9. a kind of synthetic method of Methoxvbenzofuran ketone according to claim 1, it is characterised in that: the synthesis side
Methoxvbenzofuran ketone concentration when terminating precipitation in method step 12 is controlled 55%.
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102241651A (en) * | 2011-05-25 | 2011-11-16 | 江苏七洲绿色化工股份有限公司 | Preparation method of azoxystrobin intermediate |
CN102417498A (en) * | 2011-08-24 | 2012-04-18 | 重庆紫光化工股份有限公司 | Synthetic method of 3-(alpha-methoxy)methylene benzofuran-2(3H)-one |
-
2019
- 2019-01-24 CN CN201910069832.1A patent/CN109678825A/en not_active Withdrawn
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102241651A (en) * | 2011-05-25 | 2011-11-16 | 江苏七洲绿色化工股份有限公司 | Preparation method of azoxystrobin intermediate |
CN102417498A (en) * | 2011-08-24 | 2012-04-18 | 重庆紫光化工股份有限公司 | Synthetic method of 3-(alpha-methoxy)methylene benzofuran-2(3H)-one |
Non-Patent Citations (1)
Title |
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周林芳等: "3-(a-甲氧基)甲烯基苯并呋喃-2(3H)-酮的合成与优化", 《农药》 * |
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Application publication date: 20190426 |
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