CN108863731A - One kind 1,2- bis-（2-（4- methylphenoxy）Ethyoxyl）The synthetic method of ethane - Google Patents
One kind 1,2- bis-（2-（4- methylphenoxy）Ethyoxyl）The synthetic method of ethane Download PDFInfo
- Publication number
- CN108863731A CN108863731A CN201810566716.6A CN201810566716A CN108863731A CN 108863731 A CN108863731 A CN 108863731A CN 201810566716 A CN201810566716 A CN 201810566716A CN 108863731 A CN108863731 A CN 108863731A
- Authority
- CN
- China
- Prior art keywords
- bis
- ethyoxyl
- ethane
- hours
- methylphenoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000010189 synthetic method Methods 0.000 title claims abstract description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 48
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims abstract description 40
- -1 4- methylphenoxy Chemical group 0.000 claims abstract description 31
- 239000007787 solid Substances 0.000 claims abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 23
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims abstract description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000001914 filtration Methods 0.000 claims abstract description 15
- 239000000843 powder Substances 0.000 claims abstract description 10
- 238000003756 stirring Methods 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000004321 preservation Methods 0.000 claims abstract description 3
- 238000010792 warming Methods 0.000 claims description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 239000002994 raw material Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 241000509404 Scorpaenichthys marmoratus Species 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 238000012805 post-processing Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- VTJUKNSKBAOEHE-UHFFFAOYSA-N calixarene Chemical class COC(=O)COC1=C(CC=2C(=C(CC=3C(=C(C4)C=C(C=3)C(C)(C)C)OCC(=O)OC)C=C(C=2)C(C)(C)C)OCC(=O)OC)C=C(C(C)(C)C)C=C1CC1=C(OCC(=O)OC)C4=CC(C(C)(C)C)=C1 VTJUKNSKBAOEHE-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 150000003983 crown ethers Chemical class 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- JZEOFPSJMBFPMS-UHFFFAOYSA-N 4-methylbenzenesulfonic acid;potassium Chemical compound [K].CC1=CC=C(S(O)(=O)=O)C=C1 JZEOFPSJMBFPMS-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- VJAGHZLYXAKQID-UHFFFAOYSA-N benzenesulfonic acid;potassium Chemical compound [K].OS(=O)(=O)C1=CC=CC=C1 VJAGHZLYXAKQID-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- GHKGUEZUGFJUEJ-UHFFFAOYSA-M potassium;4-methylbenzenesulfonate Chemical compound [K+].CC1=CC=C(S([O-])(=O)=O)C=C1 GHKGUEZUGFJUEJ-UHFFFAOYSA-M 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C41/14—Preparation of ethers by exchange of organic parts on the ether-oxygen for other organic parts, e.g. by trans-etherification
-
- 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
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses one kind 1,2- bis- (2- (4- methylphenoxy) ethyoxyl) ethane synthetic methods, include the following steps：(1) 20 DEG C of stirring, 4- methylphenol and triethylene-glycol are added in n,N-Dimethylformamide, add potassium hydroxide, and 150 DEG C of reactions are poured into water standing for 24 hours for 24 hours, by reaction solution, brown solid is obtained by filtration；(2) brown solid is dissolved in ether, heated up 35 DEG C, filter off insoluble matter, be cooled to -15 DEG C, for 24 hours, filtering obtains pale yellow powder shape solid 1,2- bis- (2- (4- methylphenoxy) ethyoxyl) ethane for heat preservation.Present invention is mainly used for the synthesis of 1,2- bis- (2- (4- methylphenoxy) ethyoxyl) ethane.
Description
Technical field
The invention belongs to energetic material fields, and in particular to one kind 1,2- bis- (2- (4- methylphenoxy) ethyoxyl) ethane
Synthetic method.
Background technique
1,2- bis- (2- (2,6- dimethyl phenoxy) ethyoxyl) ethane is a kind of important chemicals, it and it derivative
Object can be used for many fields.Wherein using its as the crown ether of structural unit be not only Coordinative Chemistry, analytical chemistry, organic chemistry and
The important research content of bioinorganic chemistry, and close connection is suffered from life science, information science, material science etc.
System.And the calixarenes developed on the basis of crown ether is then former by the oxygen of rich pi-electron, adjustable three-dimensional lumen and annular array
Son, not only can complex ion but also can inclusion neutral molecule.More importantly, the readily selected sex modification of upper lower edge of calixarenes, it can
Largely there is " pre-organized structure " (Pre- for " structure platform " (Platform orbuilding block) synthesis with it
Organized structure) host molecule.
2000, Cabezon etc. selected 4- methylphenol and triethylene-glycol p-methyl benzenesulfonic acid ester is raw material, potassium carbonate
Compound 1 has been synthesized under lithium bromide catalysis, 2- bis- (2- (4- methylphenoxy) ethyoxyl) ethane, (B.Cabezon,
J.Cao,F.M.Raymo.Self-complementary[2]catenanes and their related[3]catenanes,
Chemistry-A European Journal,2000,6(12),2262-2273.).The following institute of the synthetic route of Cabezon method
Show：
Cabezon method is raw material using triethylene-glycol p-methyl benzenesulfonic acid ester, and triethylene-glycol p-methyl benzenesulfonic acid
Ester will increase reaction step by triethylene glycol and the condensation preparation of p-methyl benzenesulfonic acid acyl chlorides；Cabezon method can generate a large amount of pairs
Product p-methyl benzenesulfonic acid potassium, potassium toluene sulfonate are not allowed easy to handle, increase the pollution of reaction；Cabezon method uses lithium bromide
For catalyst, price is higher；The Cabezon method reaction time is longer, needs 72h；Cabezon method post-processing operation is complicated, needs
Final product can be just obtained by column chromatography for separation, total recovery is lower, and only 78%.
Summary of the invention
The technical problem to be solved by the present invention is to overcome the deficiencies in the prior art, a kind of reaction step is provided
Less, post-processing approach is clear, higher 1,2- bis- (2- (4- methylphenoxy) ethyoxyl) the ethane synthetic method of reaction yield.
Synthetic route of the invention is using 4- methylphenol and triethylene-glycol as raw material, using potassium hydroxide as catalyst,
Acetonitrile is solvent, carries out etherification reaction using post-processing and obtains product 1,2- bis- (2- (4- methylphenoxy) ethyoxyl) second
Alkane.
The synthetic method of one kind 1,2- bis- (2- (4- methylphenoxy) ethyoxyl) ethane of the invention, 1,2- bis- (2- (4-
Methylphenoxy) ethyoxyl) ethane structural formula such as shown in (I)：
Using 4- methylphenol and triethylene-glycol as raw material, such as (II) and (III) is shown respectively for structural formula, including with
Lower step：
(1) under 20 DEG C~30 DEG C of temperature stirrings, 4- methylphenol and triethylene-glycol are added in acetonitrile, are added
Into solvent, then potassium hydroxide is added thereto, is 130 DEG C~160 DEG C reaction for 24 hours~36h in temperature, reaction solution is poured into
For 24 hours~48h is stood in water, and brown solid is obtained by filtration；Wherein, solvent be dimethyl sulfoxide or n,N-Dimethylformamide, two
Contracting triethylene glycol, 4- methylphenol, potassium hydroxide mass ratio be 1:1.58~1.73:3.00~3.50；
(2) brown solid is dissolved in ether, is warming up to 30 DEG C~35 DEG C, filters off insoluble matter while hot, be cooled to -15 DEG C~-
10 DEG C, for 24 hours~48h is kept the temperature, filtering solution obtains pale yellow powder shape solid 1,2- bis- (2- (4- methylphenoxy) ethyoxyl)
Ethane.A kind of synthetic method of currently preferred 1,2- bis- (2- (4- methylphenoxy) ethyoxyl) ethane, including following step
Suddenly：
Under (1) 20 DEG C of stirring, 4- methylphenol and triethylene-glycol are added in n,N-Dimethylformamide, then to
Potassium hydroxide is wherein added, is 150 DEG C in temperature and reacts for 24 hours, reaction solution is poured into water standing for 24 hours, brown is obtained by filtration
Solid 1, wherein triethylene-glycol, 4- methylphenol, potassium hydroxide mass ratio be 1:1.60:0.72；
(2) brown solid is dissolved in ether, is warming up to 35 DEG C, filters off insoluble matter while hot, be cooled to -10 DEG C~-15 DEG C, protected
For 24 hours, filtering solution obtains pale yellow powder shape solid 1,2- bis- (2- (4- methylphenoxy) ethyoxyl) ethane to temperature.
Advantages of the present invention：
(1) reaction step of the present invention is simple, is directly condensed to yield product using triethylene-glycol and 4- methylphenol, and
Documents replace to obtain product to triethylene-glycol p-methyl benzenesulfonic acid ester using 4- methylphenol, and triethylene-glycol pair
Tosylate will pass through triethylene glycol and the condensation preparation of p-methyl benzenesulfonic acid acyl chlorides；
(2) by-product that the present invention generates is potassium chloride, is easily processed, and documents can generate a large amount of by-products to first
Benzene sulfonic acid potassium, it is not easy to handle；The clear simplicity of post-processing approach of the present invention, after pouring into aqueous solution crystallization, Diethyl ether recrystallization,
Purity reaches 99% or more, and documents need just obtain final product by column chromatography for separation, and post-processing is complicated；
(3) present invention is catalyst using cheap potassium hydroxide, and documents are using lithium bromide costly
Catalyst increases cost；Synthetic method yield of the invention is higher, and the total recovery of reaction can reach 86.48%, and compare text
Yield in part is 78%.
Specific embodiment
The present invention is described in further details below with reference to embodiment.
Embodiment 1
Under 20 DEG C of temperature stirrings, 1.60g 4- methylphenol and 1g triethylene-glycol are added to 10ml N, N- bis-
In methylformamide, potassium hydroxide 0.72g is added to it, is warming up to 150 DEG C, after reaction for 24 hours, reaction solution is poured into 1L water
It stands for 24 hours, brown solid is obtained by filtration.
Brown solid is dissolved in 5ml ether, is warming up to 35 DEG C, filters off insoluble matter, is cooled to -15 DEG C, keeps the temperature 48h, filters molten
Liquid, obtains 1.53g pale yellow powder shape solid 1,2- bis- (2- (4- methylphenoxy) ethyoxyl) ethane, and yield 86.48% is pure
Degree 99.11%, 66 DEG C -67 DEG C of fusing point.
Structural Identification：
IR(KBr)ν:3444,3100,3063,3022,2928,2923,2897,2859,2733,2681,2590,2545,
2483,2358,2129,2067,1993,1877,1766,1612,1585,1510,1488,1454,1412,1374,1321,
1298,1248,1181,1138,1112,1070,1041,1013,1000,966,928,875,853,810,740,585,560,
510cm-l.
1H NMR(CDCl3-d6):δ7.04(4H,t),6.79(4H,d),4.08(4H,t),3.83(4H,s),3.81(4H,
t),2.27(6H,t)；
13C NMR(CDCl3-d6)δ156.74,130.05,129.87,114.61,69.91,67.34,65.85,20.48
Elemental analysis：Molecular formula C20H26O4
Theoretical value：C,72.70；H,7.93；O,19.37.
Measured value：C,72.27；H,7.77；O,19.96.
Above structure appraising datum confirms that the substance that this step obtains is strictly (2- (4- methylphenoxy) ethoxy of 1,2- bis-
Base) ethane.
Embodiment 2
Under 20 DEG C of temperature stirrings, 1.70g 4- methylphenol and 1g triethylene-glycol are added to 10ml N, N- bis-
In methylformamide, potassium hydroxide 0.72g is added to it, is warming up to 150 DEG C, after reaction for 24 hours, reaction solution is poured into 1L water
It stands for 24 hours, brown solid is obtained by filtration.
Brown solid is dissolved in 5ml ether, is warming up to 35 DEG C, filters off insoluble matter, is cooled to -15 DEG C, keeps the temperature 48h, filters molten
Liquid, obtains 1.52g pale yellow powder shape solid 1,2- bis- (2- (4- methylphenoxy) ethyoxyl) ethane, and yield 85.88% is pure
Degree 98.78%, 66 DEG C -67 DEG C of fusing point.
Embodiment 3
Under 20 DEG C of temperature stirrings, 1.60g 4- methylphenol and 1g triethylene-glycol are added to 10ml N, N- bis-
In methylformamide, potassium hydroxide 0.72g is added to it, is warming up to 140 DEG C, after reaction for 24 hours, reaction solution is poured into 1L water
It stands for 24 hours, brown solid is obtained by filtration.
Brown solid is dissolved in 5ml ether, is warming up to 35 DEG C, filters off insoluble matter, is cooled to -15 DEG C, keeps the temperature 48h, filters molten
Liquid, obtains 1.50g pale yellow powder shape solid, 2- bis- (2- (4- methylphenoxy) ethyoxyl) ethane, and yield 84.75% is pure
Degree 98.42%, 66 DEG C -67 DEG C of fusing point.
Embodiment 4
Under 20 DEG C of temperature stirrings, 1.60g 4- methylphenol and 1g triethylene-glycol are added to 10ml N, N- bis-
In methylformamide, potassium hydroxide 0.72g is added to it, is warming up to 150 DEG C, after reaction for 24 hours, reaction solution is poured into 1L water
It stands for 24 hours, brown solid is obtained by filtration.
Brown solid is dissolved in 5ml ether, is warming up to 35 DEG C, filters off insoluble matter, is cooled to -15 DEG C, heat preservation for 24 hours, is filtered molten
Liquid, obtains 1.51g pale yellow powder shape solid 1,2- bis- (2- (4- methylphenoxy) ethyoxyl) ethane, and yield 85.31% is pure
Degree 98.21%, 66 DEG C -67 DEG C of fusing point.
Embodiment 5
Under 20 DEG C of temperature stirrings, 1.60g 4- methylphenol and 1g triethylene-glycol are added to 10ml N, N- bis-
In methylformamide, potassium hydroxide 0.72g is added to it, is warming up to 150 DEG C, after reaction for 24 hours, reaction solution is poured into 1L water
It stands for 24 hours, brown solid 1 is obtained by filtration.
Brown solid is dissolved in 5ml ether, is warming up to 35 DEG C, filters off insoluble matter, is cooled to -10 DEG C, keeps the temperature 48h, filters molten
Liquid, obtains 1.55g pale yellow powder shape solid 1,2- bis- (2- (4- methylphenoxy) ethyoxyl) ethane, and yield 87.57% is pure
Degree 95.24%, 66 DEG C -67 DEG C of fusing point.
Claims (2)
1. one kind 1, the synthetic method of 2- bis- (2- (4- methylphenoxy) ethyoxyl) ethane, 1,2- bis- (2- (4- methylenedioxy phenoxy
Base) ethyoxyl) ethane structural formula such as shown in (I)：
Using 4- methylphenol and triethylene-glycol as raw material, such as (II) and (III) is shown respectively for structural formula, including following step
Suddenly：
(1) under 20 DEG C~30 DEG C of temperature stirrings, 4- methylphenol and triethylene-glycol is added in acetonitrile, are added to molten
In agent, then potassium hydroxide is added thereto, is 130 DEG C~160 DEG C reaction for 24 hours~36h in temperature, reaction solution is poured into water
For 24 hours~48h is stood, brown solid is obtained by filtration；Wherein, solvent is dimethyl sulfoxide or n,N-Dimethylformamide, two contractings three
Ethylene glycol, 4- methylphenol, potassium hydroxide mass ratio be 1:1.58~1.73:3.00~3.50；
(2) brown solid is dissolved in ether, is warming up to 30 DEG C~35 DEG C, filters off insoluble matter while hot, is cooled to -15 DEG C~-10 DEG C,
For 24 hours~48h is kept the temperature, filtering solution obtains pale yellow powder shape solid 1,2- bis- (2- (4- methylphenoxy) ethyoxyl) ethane.
2. a kind of synthetic method of 1,2- bis- (2- (4- methylphenoxy) ethyoxyl) ethane according to claim 1, packet
Include following steps：
Under (1) 20 DEG C of stirring, 4- methylphenol and triethylene-glycol are added in n,N-Dimethylformamide, then thereto
Potassium hydroxide is added, is 150 DEG C in temperature and reacts for 24 hours, reaction solution is poured into water standing for 24 hours, brown solid is obtained by filtration
1, wherein triethylene-glycol, 4- methylphenol, potassium hydroxide mass ratio be 1:1.60:0.72；
(2) brown solid is dissolved in ether, is warming up to 35 DEG C, filters off insoluble matter while hot, be cooled to -10 DEG C~-15 DEG C, heat preservation
For 24 hours, filtering solution obtains pale yellow powder shape solid 1,2- bis- (2- (4- methylphenoxy) ethyoxyl) ethane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810566716.6A CN108863731A (en) | 2018-06-05 | 2018-06-05 | One kind 1,2- bis-（2-（4- methylphenoxy）Ethyoxyl）The synthetic method of ethane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810566716.6A CN108863731A (en) | 2018-06-05 | 2018-06-05 | One kind 1,2- bis-（2-（4- methylphenoxy）Ethyoxyl）The synthetic method of ethane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN108863731A true CN108863731A (en) | 2018-11-23 |
Family
ID=64335283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810566716.6A Pending CN108863731A (en) | 2018-06-05 | 2018-06-05 | One kind 1,2- bis-（2-（4- methylphenoxy）Ethyoxyl）The synthetic method of ethane |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108863731A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107935822A (en) * | 2017-11-24 | 2018-04-20 | 西安近代化学研究所 | 1,2 two（2‑（4 methoxyphenoxies）Ethyoxyl）The preparation method of ethane |
| CN108002988A (en) * | 2017-11-24 | 2018-05-08 | 西安近代化学研究所 | 1,2- bis-（2-（2,6- dimethoxy phenoxy groups）Ethyoxyl）The preparation method of ethane |
-
2018
- 2018-06-05 CN CN201810566716.6A patent/CN108863731A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107935822A (en) * | 2017-11-24 | 2018-04-20 | 西安近代化学研究所 | 1,2 two（2‑（4 methoxyphenoxies）Ethyoxyl）The preparation method of ethane |
| CN108002988A (en) * | 2017-11-24 | 2018-05-08 | 西安近代化学研究所 | 1,2- bis-（2-（2,6- dimethoxy phenoxy groups）Ethyoxyl）The preparation method of ethane |
Non-Patent Citations (7)
| Title |
|---|
| B.CABEZON: "Self-complementary [2]catenanes and their related [3]catenanes", 《CHEMISTRY-A EUROPEAN JOURNAL》 * |
| D H MORE: "Microwave-assisted solvent-free o-alkylation and acylation of thymol and geraniol using fly ash as solid support", 《JOURNAL OF SCIENTIFIC & INDUSTRIAL RESEARCH》 * |
| O.N.CHUPAKHIN: "O.N.Chupakhin New 1,2,4-triazine-containing podands synthesis and properties", 《RUSSIAN CHEMICAL BULLETIN, INTERNATIONAL EDITION》 * |
| 信颖: "《有机化学 供中药学、药学、制药工程等专业用 新世纪第4版》", 31 January 2017 * |
| 荣国斌: "《高等有机化学》", 31 October 2007 * |
| 邢其毅: "《基础有机化学 上》", 30 June 1980 * |
| 陈碧芬: "《应用有机化学》", 31 May 2012 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108659041B (en) | Phosphine ligand compounds based on tetramethylspirodihydroindene skeleton, intermediates, preparation methods and uses thereof | |
| CN106242971A (en) | A kind of chloracetate synthesis in water technology and the new method of preparation 2,4 D esters thereof | |
| CN104250232A (en) | Preparation method of parecoxib sodium | |
| CN107686471A (en) | A kind of Fei Luokao former times and its synthetic method of intermediate | |
| CN108503564A (en) | A kind of Mivacurium Chloride intermediate and the method using intermediate synthesis Mivacurium Chloride | |
| CN106146457B (en) | 5-chloro-2-acyl chloride thiophene intermediate and preparation method thereof | |
| CN108863731A (en) | One kind 1,2- bis-（2-（4- methylphenoxy）Ethyoxyl）The synthetic method of ethane | |
| CN101260092B (en) | Method for preparing cinepazide maleate | |
| CN101218218A (en) | New pyrocatechin derivatives | |
| CN104829465A (en) | Method for preparing 4-isopropamide group-1-butanol | |
| Suzuki et al. | Preparation of aromatic iodides from bromides via the reverse halogen exchange | |
| CN108558613A (en) | One kind 1,2- bis-（2-（2,6- dimethyl phenoxies）Ethyoxyl）The preparation method of ethane | |
| CN108558615A (en) | 1,2- bis-（2-（2,6- dimethyl phenoxies）Ethyoxyl）The synthetic method of ethane | |
| CN108586209A (en) | One kind 1,2- bis-（2-（2,6- dimethyl phenoxies）Ethyoxyl）The synthetic method of ethane | |
| CN108558616A (en) | One kind 1,2- bis-（2-（4- methylphenoxies）Ethyoxyl）The preparation method of ethane | |
| CN108558617A (en) | 1,2- bis-（2-（4- methylphenoxies）Ethyoxyl）The preparation method of ethane | |
| CN108821954A (en) | 1,2- bis-（2-（4- methylphenoxy）Ethyoxyl）The synthetic method of ethane | |
| CN107540655A (en) | A kind of new preparation S（Perfluoroalkyl）The method of dibenzothiophenes fluoroform sulphonate | |
| CN108558614A (en) | 1,2- bis-（2-（2,6- dimethyl phenoxies）Ethyoxyl）The preparation method of ethane | |
| CN101550097A (en) | Preparation method of 5-chlorosulfonyl isophthaloyl acid chloride | |
| CN109265385B (en) | Synthesis process of chiral catalyst | |
| CN109134342B (en) | A kind of preparation method of 3,4-disubstituted pyrrole | |
| CN102924349B (en) | Method for preparing bis (4-tert-butyl benzyl) sulfide product | |
| CN109678750A (en) | A kind of preparation method of N, N- diethyl -2- hydroxyl -2- phenyl acetamide | |
| CN103102308B (en) | Method of preparing pyraoxystrobin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20181123 |