CN107311922A - A kind of synthetic method of third pyrrole ether - Google Patents
A kind of synthetic method of third pyrrole ether Download PDFInfo
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- CN107311922A CN107311922A CN201710788988.6A CN201710788988A CN107311922A CN 107311922 A CN107311922 A CN 107311922A CN 201710788988 A CN201710788988 A CN 201710788988A CN 107311922 A CN107311922 A CN 107311922A
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- Prior art keywords
- pyrrole ether
- potassium hydroxide
- ether
- reacts
- obtains
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The present invention relates to a kind of synthetic method of third pyrrole ether, its synthetic route is made up of three-step reaction：（1）Phenol reacts with parachlorophenol in the presence of potassium hydroxide and toluene obtains p-phenoxyphenol；（2）P-phenoxyphenol reacts with expoxy propane in the presence of potassium hydroxide obtains 1（4 phenoxy-phenoxies）2 propyl alcohol；（3）1‑（4 phenoxy-phenoxies）2 propyl alcohol and 2 chloropyridines react in the presence of potassium hydroxide and toluene obtains the third pyrrole ether.The advantage of the invention is that：Third pyrrole ether is the insect growth regulator, IGR that phenylate class upsets insect growth, belongs to the novel pesticide of juvenoid, with interior suction transfer activity, low toxicity, and the lasting period is long, to crop safety, to fish low toxicity, the characteristics of small to eco-environmental impact；The comparison of processes is easy, it is easy to industrialized production.
Description
Technical field
The present invention relates to organic chemistry filed, more particularly to a kind of synthetic method of third pyrrole ether.
Background technology
Third pyrrole ether is the insect growth regulator, IGR that phenylate class upsets insect growth, belongs to the new type disinsection of juvenoid
Agent, with interior suction transfer activity, low toxicity, the lasting period is long, to crop safety, to fish low toxicity, the spy small to eco-environmental impact
Point；There is good prevention effect to Bemisia tabaci, scale insect, diamondback moth, beet armyworm, prodenia litura, pear psyllid, thrips etc.,
This product has good prevention effect to sanitary insect pests such as fly, mosquitoes simultaneously, is pupated and sprout wings work with mosquito, fly larvae is suppressed
With；Mosquito, fly larvae contact the medicament, are substantially all dead in pupa time, it is impossible to sprout wings；The medicament lasting period is up to 1 month or so,
And easy to use, free from extraneous odour, it is preferable mosquito eradication, fly medicine.
So, the synthesis of the third pyrrole ether is just most important.And the synthetic method of existing third pyrrole ether, method is all cumbersome, no
It is easy to industrialized production.
The content of the invention
The technical problem to be solved in the present invention is to provide the synthesis side of the third pyrrole ether that is a kind of easy and being easy to industrialized production
Method.
In order to solve the above technical problems, the technical scheme is that：A kind of conjunction of third pyrrole ether
Into method, its innovative point is：Its synthetic route is made up of three-step reaction：
（1）Phenol reacts with parachlorophenol in the presence of potassium hydroxide and toluene obtains p-phenoxyphenol；
（2）P-phenoxyphenol reacts with expoxy propane in the presence of potassium hydroxide obtains 1-（4- phenoxy-phenoxies）2- third
Alcohol；
（3）1-（4- phenoxy-phenoxies）2- propyl alcohol reacts with 2- chloropyridines in the presence of potassium hydroxide and toluene obtains the third pyrrole
Ether.
The synthetic route of above-mentioned reaction is：
1st, POP synthesis
；
2nd, PPP synthesis
；
3rd, the synthesis of the third pyrrole ether
。
Further, the trade name of the third described pyrrole ether is Nylar, and chemical name is 4- benzene oxygen aldehyde phenyl（RS）-
〔2-（2- pyridine radicals oxygen-propyl group）) ether, molecular formula is C20H19NO3,Structural formula is,
Relative molecular mass is 321, and sterling is white crystals.
The advantage of the invention is that：
（1）Third pyrrole ether is the insect growth regulator, IGR that phenylate class upsets insect growth, belongs to the new type disinsection of juvenoid
Agent, with interior suction transfer activity, low toxicity, the lasting period is long, to crop safety, to fish low toxicity, the spy small to eco-environmental impact
Point；
（2）The comparison of processes is easy, it is easy to industrialized production.
Brief description of the drawings
The present invention is further detailed explanation with reference to the accompanying drawings and detailed description.
Fig. 1 is POP synthesis process flow diagram.
Fig. 2 is the synthesis process flow diagram of the third pyrrole ether.
Embodiment
As depicted in figs. 1 and 2, specific production craft step is as follows：
1st, POP synthesis
Toluene 1600Kg, phenol 440Kg, potassium hydroxide 275KG is put into reactor successively, heating, backflow band water, extremely arrives kettle temperature
Up to more than 110 DEG C bands to anhydrous；Toluene is steamed to the greatest extent, catalyst copper powder 10Kg is disposably added in reactor, is heated up, in 140
DEG C when, be added dropwise parachlorophenol 600Kg, dropping temperature control at 140-150 DEG C, time for adding about 4 hours or so is dripped off, herein
At a temperature of insulation reaction more than 10 hours, sampling parachlorophenol ＜ 1%, reaction terminates；POP is steamed using vacuum distillation：782Kg
(content 98%, yield：90%, in terms of parachlorophenol)；
2nd, PPP synthesis
By water 2000Kg, potassium hydroxide 247Kg, POP：In 782Kg input reactors, stirring is opened, epoxy third is added dropwise in 10-20 DEG C
Alkane 240Kg, about 3 hours, completion of dropping was reacted 2 hours, sampling analysis is qualified to POP≤1%；
3rd, the synthesis of the third pyrrole ether
Toluene 3000Kg is added, 50 degree of branch vibration layers are warming up to, 247Kg potassium hydroxide is added, stirring is heated to 80 degree, dropwise addition
2- chloropyridines:477Kg, continues insulation reaction to terminal, separates oil reservoir, be washed to neutrality, precipitation, residue is obtained with recrystallizing methanol
White solid, 1190Kg；47.0~48.0 DEG C of fusing point, yield 85.5%, content 97.2%.
The general principle and principal character and advantages of the present invention of the present invention has been shown and described above.The skill of the industry
Art personnel are it should be appreciated that the present invention is not limited to the above embodiments, and described in above-described embodiment and specification is explanation
The principle of the present invention, without departing from the spirit and scope of the present invention, various changes and modifications of the present invention are possible, these
Changes and improvements all fall within the protetion scope of the claimed invention.The claimed scope of the invention by appended claims and
Its equivalent thereof.
Claims (2)
1. a kind of synthetic method of third pyrrole ether, it is characterised in that its synthetic route is made up of three-step reaction：
（1）Phenol reacts with parachlorophenol in the presence of potassium hydroxide and toluene obtains p-phenoxyphenol；
（2）P-phenoxyphenol reacts with expoxy propane in the presence of potassium hydroxide obtains 1-（4- phenoxy-phenoxies）2- third
Alcohol；
（3）1-（4- phenoxy-phenoxies）2- propyl alcohol reacts with 2- chloropyridines in the presence of potassium hydroxide and toluene obtains the third pyrrole
Ether.
2. a kind of synthetic method of third pyrrole ether according to claim 1, it is characterised in that：The trade name of the third described pyrrole ether
Title is Nylar, and chemical name is 4- benzene oxygen aldehyde phenyl（RS）-〔2-（2- pyridine radicals oxygen-propyl group）) ether, molecular formula is
C20H19NO3,Structural formula is, relative molecular mass is 321, and sterling is white crystals.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710788988.6A CN107311922A (en) | 2017-09-05 | 2017-09-05 | A kind of synthetic method of third pyrrole ether |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710788988.6A CN107311922A (en) | 2017-09-05 | 2017-09-05 | A kind of synthetic method of third pyrrole ether |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN107311922A true CN107311922A (en) | 2017-11-03 |
Family
ID=60177449
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710788988.6A Pending CN107311922A (en) | 2017-09-05 | 2017-09-05 | A kind of synthetic method of third pyrrole ether |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108276255A (en) * | 2018-02-08 | 2018-07-13 | 盐城辉煌化工有限公司 | The method for selective synthesis of Nylar intermediate ether alcohol |
| CN111153772A (en) * | 2020-01-08 | 2020-05-15 | 安徽禾宸化学科技有限公司 | Preparation method for constructing diphenyl ether structure compound |
| CN113429268A (en) * | 2021-06-18 | 2021-09-24 | 浙江禾本科技股份有限公司 | Synthetic method of 4-phenoxyphenol |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107266358A (en) * | 2017-06-21 | 2017-10-20 | 南通施壮化工有限公司 | A kind of Nylar active compound synthetic method |
-
2017
- 2017-09-05 CN CN201710788988.6A patent/CN107311922A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107266358A (en) * | 2017-06-21 | 2017-10-20 | 南通施壮化工有限公司 | A kind of Nylar active compound synthetic method |
Non-Patent Citations (1)
| Title |
|---|
| 何锡辉等: ""蚊蝇醚的合成工艺研究"", 《西华大学学报· 自然科学版》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108276255A (en) * | 2018-02-08 | 2018-07-13 | 盐城辉煌化工有限公司 | The method for selective synthesis of Nylar intermediate ether alcohol |
| CN111153772A (en) * | 2020-01-08 | 2020-05-15 | 安徽禾宸化学科技有限公司 | Preparation method for constructing diphenyl ether structure compound |
| CN113429268A (en) * | 2021-06-18 | 2021-09-24 | 浙江禾本科技股份有限公司 | Synthetic method of 4-phenoxyphenol |
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