CN101157614A - Chemical method for synthesizing 6,8-dichloro ethyl cacodylic acid caprylate - Google Patents
Chemical method for synthesizing 6,8-dichloro ethyl cacodylic acid caprylate Download PDFInfo
- Publication number
- CN101157614A CN101157614A CNA2007101562171A CN200710156217A CN101157614A CN 101157614 A CN101157614 A CN 101157614A CN A2007101562171 A CNA2007101562171 A CN A2007101562171A CN 200710156217 A CN200710156217 A CN 200710156217A CN 101157614 A CN101157614 A CN 101157614A
- Authority
- CN
- China
- Prior art keywords
- trichloromethyl
- hydroxyl
- octylate
- ethyl octylate
- dichloro
- 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.)
- Granted
Links
Abstract
The invention discloses a chemical synthetic method for 6, 8-ethyl octylate chloride. The method comprises the steps as follows: 6-hydroxyl-8-ethyl octylate chloride is dissolved in N, N-dimethylformamide; solution which is dissolved with organic solution of double (trichloride trichloromethyl)-carbonic acid ester is dropped in when in mixing under the cold water bath condition; the solution is gradually warmed to 50 to 90 DEG C for reacting for 2 to 8 hours after dropping; and the reaction solution is disposed into 6, 8-ethyl octylate chloride after finishing the reaction. As the invention replaces sulphoxides chloride with double (trichloride trichloromethyl)-carbonic acid ester, the invention produces environment friendly Vilsmeier agent which needs not to be separated in the reaction, and the Vilsmeier agent directly reacts with 6-hydroxyl-8-ethyl octylate chloride to produce 6, 8-ethyl octylate chloride. Besides, the invention has the advantages of advanced art, rational technological condition, simple and safe operation, high reaction yield, low production cost, low three-waste emission as well as great implementation value and social and economic efficiency.
Description
(1) technical field
The present invention relates to a kind ofly 6, the chemical synthesis process of 8-dichloro ethyl octylate is particularly with two (trichloromethyl) carbonic ethers and 6-hydroxyl-8-chloroctanoic acid ethyl ester and N, dinethylformamide prepared in reaction 6, the chemical synthesis process of 8-dichloro ethyl octylate.
(2) background technology
6,8-dichloro ethyl octylate is the important organic intermediate that is used for synthetic Thioctic Acid.Thioctic Acid is called as " universal antioxidant ", is widely used in multiple diseases such as treatment and preventing heart disease, diabetes, degenerative brain disorder, and domestic and world market has a extensive future.
Before the present invention provided, in the prior art 6, mostly the chemical synthesis process of 8-dichloro ethyl octylate was to prepare with 6-hydroxyl-8-chloroctanoic acid ethyl ester and sulfur oxychloride chloro.As document [Zhuranl Obshchei Khimii, 1964,34,3662] reported described 6-hydroxyl-8-chloroctanoic acid ethyl ester and sulfur oxychloride in the presence of the catalytic amount pyridine in benzene back flow reaction 1h and generate 6,8-dichloro ethyl octylate (crude product yield 88%), contain a large amount of asphyxiant sulfurous gas (national environmental protection is to one of strict six indexs controlling of atmosphere) in this process tail gas, difficult treatment, the main at present mixture that adopts alkali to absorb preparation S-WAT and sodium-chlor, but there is big problem in market sale, and, after absorbing with alkali is the aqueous solution, just can obtain the mixture of S-WAT and sodium-chlor after must concentrating, the production process energy consumption is very big, and production cost is higher.The transportation of sulfur oxychloride and use are strictly controlled in addition, to conversion unit sealing requirements height, invest also bigger, also there is the catalyzer pyridine in former technology of while, and the smell is awful, operating environment is very abominable, problems such as the strict at present restriction of reaction solvent benzene China is used, and product yield and purity are lower need to solve.
(3) summary of the invention
The technical problem to be solved in the present invention provide that a kind of technology is simple, production safety is reliable, reaction yield is high, cost is low, the three wastes are little 6, the chemical synthesis process of 8-dichloro ethyl octylate.
The technical solution used in the present invention is as follows: 6-hydroxyl-8-chloroctanoic acid ethyl ester is dissolved in N, in the dinethylformamide, under agitation drip the solution of the organic solvent that is dissolved with two (trichloromethyl) carbonic ethers under the ice-water bath condition, drip off and slowly be warming up to 50～80 ℃ of reactions 2～8 hours, react the reaction solution that finishes and get 6 through aftertreatment, 8-dichloro ethyl octylate.Reaction equation is as follows:
Described 6-hydroxyl-8-chloroctanoic acid ethyl ester: two (trichloromethyl) carbonic ether: N, the amount of substance ratio of dinethylformamide is 1: 0.34～1.0: 1.0～3.0.
Described organic solvent is the mixture of following one or more arbitrary proportions: benzene, toluene, chlorobenzene, normal hexane, hexanaphthene, ethyl acetate, trichloromethane, ethylene dichloride.
The consumption of described organic solvent is 1.5～3 times of two (trichloromethyl) carbonic ether quality.
Further, described 6-hydroxyl-8-chloroctanoic acid ethyl ester: two (trichloromethyl) carbonic ether: N, the amount of substance ratio of dinethylformamide be preferably 1: 0.34～and 0.5: 1.0～1.5.
Described organic solvent is preferably the mixture of following one or more arbitrary proportions: chlorobenzene, toluene, ethylene dichloride.
Described aftertreatment is: reaction solution is cooled to be neutralized to neutrality with alkali lye below 30 ℃, and normal pressure boils off solvent, and it is described 6 that vacuum distilling gets, 8-dichloro ethyl octylate.
Concrete recommendation described 6, the chemical synthesis process of 8-dichloro ethyl octylate carries out according to following steps: according to 6-hydroxyl-8-chloroctanoic acid ethyl ester: two (trichloromethyl) carbonic ether: N, the amount of substance ratio of dinethylformamide is 1: 0.34～0.5: 1.0～1.5 to feed intake, 6-hydroxyl-8-chloroctanoic acid ethyl ester is dissolved in N, in the dinethylformamide, under agitation drip the solution of the organic solvent that is dissolved with two (trichloromethyl) carbonic ethers under the ice-water bath condition, be warmed up to 50～80 ℃ of reactions 2～8 hours after dripping off, reacting the afterreaction liquid that finishes is cooled to below 30 ℃, be neutralized to neutrality with alkali lye, normal pressure boils off solvent, and vacuum distilling gets 6,8-dichloro ethyl octylate; Described organic solvent is chlorobenzene or toluene, and the quality of described organic solvent is 1.5～3 times of two (trichloromethyl) carbonic ether quality.
It is 5mmHg that described vacuum distilling refers to collect vacuum tightness, and temperature is 172～176 ℃ a cut, promptly 6, and 8-dichloro ethyl octylate (C
10H
18Cl
2O
2).
In reaction process, specifically can according to whether also have hydrogenchloride to generate and judge reaction end.
The present invention compared with prior art, its beneficial effect is embodied in:
The present invention substitutes sulfur oxychloride with two (trichloromethyl) carbonic ether, in reaction, generate and need not isolating environment amenable Vilsmeier reagent, direct and 6-hydroxyl-8-chloroctanoic acid ethyl ester generation chlorination gets 6,8-dichloro ethyl octylate, operational path advanced person, processing condition are reasonable, safety simple to operate, the reaction yield height, production cost is lower, the three wastes are little, have bigger implementary value and economic results in society.
(4) embodiment:
Below with specific embodiment technical scheme of the present invention is described, but protection scope of the present invention is not limited thereto:
Embodiment 1
Feed intake amount of substance than 6-hydroxyl-8-chloroctanoic acid ethyl ester: two (trichloromethyl) carbonic ether: N, dinethylformamide is 1: 0.34: 1.2, the organic solvent of two (trichloromethyl) carbonic ethers of dissolving is a toluene, and its consumption is about 2 times of two (trichloromethyl) carbonic ether quality.
Thermometer is being housed, in reflux condensing tube and the churned mechanically 250mL there-necked flask, 6-hydroxyl-8-chloroctanoic acid ethyl ester 44.5g (200mmol) is dissolved in N, among the dinethylformamide 17.5g (240mmol), ice-water bath also stirs the organic solution that drips two (trichloromethyl) carbonic ethers down (will two (trichloromethyl) carbonic ether 20.2g (68mmol) be dissolved in 40g toluene formulated), drip off and slowly be warming up to 50 ℃, and at 50～55 ℃ of reaction 8h, be cooled to be neutralized to neutrality with alkali lye below 30 ℃, normal pressure boils off solvent, vacuum tightness gets 6 for the cut of 172-176 ℃ of 5mm mercury column distillation collection, 8-dichloro ethyl octylate 43.67g, molar product yield 90.6%, purity 98.1%.
Embodiment 2
Feed intake amount of substance than 6-hydroxyl-8-chloroctanoic acid ethyl ester: two (trichloromethyl) carbonic ether: N, dinethylformamide is 1: 0.4: 1.2,6-hydroxyl-8-chloroctanoic acid ethyl ester charging capacity is 44.5g (200mmol), two (trichloromethyl) carbonic ether charging capacity is 23.74g (80mmol), N, the dinethylformamide charging capacity is 17.5g (240mmol), and the organic solvent of two (trichloromethyl) carbonic ethers of dissolving is a toluene, and its consumption is about 1.5 times of two (trichloromethyl) carbonic ether quality.
Temperature of reaction is 55～60 ℃, and the reaction times is 7h, and other is operated with embodiment 1, gets 6,8-dichloro ethyl octylate 44.4g, molar product yield 92.2%, purity 98.2%.
Embodiment 3
Feed intake amount of substance than 6-hydroxyl-8-chloroctanoic acid ethyl ester: two (trichloromethyl) carbonic ether: N, dinethylformamide is 1: 0.4: 1.2,6-hydroxyl-8-chloroctanoic acid ethyl ester charging capacity is 44.5g (200mmol), two (trichloromethyl) carbonic ether charging capacity is 23.7g (80mmol), N, the dinethylformamide charging capacity is 17.5g (120mmol), and the organic solvent of two (trichloromethyl) carbonic ethers of dissolving is a toluene, and its consumption is about 2 times of two (trichloromethyl) carbonic ether quality.
Temperature of reaction is 70～75 ℃, and the reaction times is 6h, and other is operated with embodiment 1, gets 6,8-dichloro ethyl octylate 45.6g, molar product yield 94.7%, purity 98.5%.
Embodiment 4
Feed intake amount of substance than 6-hydroxyl-8-chloroctanoic acid ethyl ester: two (trichloromethyl) carbonic ether: N, dinethylformamide is 1: 0.5: 1.5,6-hydroxyl-8-chloroctanoic acid ethyl ester charging capacity is 44.5g (200mmol), two (trichloromethyl) carbonic ether charging capacity is 29.7g (100mmol), N, the dinethylformamide charging capacity is 21.9g (300mmol), and the organic solvent of two (trichloromethyl) carbonic ethers of dissolving is a chlorobenzene, and its consumption is about 2 times of two (trichloromethyl) carbonic ether quality.
Temperature of reaction is 70～75 ℃, and the reaction times is 5h, and other is operated with embodiment 1, gets 6,8-dichloro ethyl octylate 45.5g, molar product yield 94.5%, purity 98.4%.
Embodiment 5
Feed intake amount of substance than 6-hydroxyl-8-chloroctanoic acid ethyl ester: two (trichloromethyl) carbonic ether: N, dinethylformamide is 1: 0.4: 1.4,6-hydroxyl-8-chloroctanoic acid ethyl ester charging capacity is 44.5g (200mmol), two (trichloromethyl) carbonic ether charging capacity is 23.7g (80mmol), N, the dinethylformamide charging capacity is 20.4g (280mmol), and the organic solvent of two (trichloromethyl) carbonic ethers of dissolving is a toluene, and its consumption is about 2 times of two (trichloromethyl) carbonic ether quality.
Temperature of reaction is 70～75 ℃, and the reaction times is 4h, and other is operated with embodiment 1, gets 6,8-dichloro ethyl octylate 45.9g, molar product yield 95.2%, purity 98.7%.
Embodiment 6
Feed intake amount of substance than 6-hydroxyl-8-chloroctanoic acid ethyl ester: two (trichloromethyl) carbonic ether: N, dinethylformamide is 1: 0.35: 1.2,6-hydroxyl-8-chloroctanoic acid ethyl ester charging capacity is 44.5g (200mmol), two (trichloromethyl) carbonic ether charging capacity is 20.8g (70mmol), N, the dinethylformamide charging capacity is 17.8g (240mmol), and the organic solvent of two (trichloromethyl) carbonic ethers of dissolving is a toluene, and its consumption is about 2 times of two (trichloromethyl) carbonic ether quality.
Temperature of reaction is 75～80 ℃, and the reaction times is 3h, and other is operated with embodiment 1, gets 6,8-dichloro ethyl octylate 45.5g, molar product yield 94.5%, purity 98.2%.
Embodiment 7
Feed intake amount of substance than 6-hydroxyl-8-chloroctanoic acid ethyl ester: two (trichloromethyl) carbonic ether: N, dinethylformamide is 1: 0.4: 1.2,6-hydroxyl-8-chloroctanoic acid ethyl ester charging capacity is 44.5g (200mmol), two (trichloromethyl) carbonic ether charging capacity is 23.74g (80mmol), N, the dinethylformamide charging capacity is 17.5g (240mmol), and the organic solvent of two (trichloromethyl) carbonic ethers of dissolving is a toluene, and its consumption is about 2.5 times of two (trichloromethyl) carbonic ether quality.
Temperature of reaction is 75～80 ℃, and the reaction times is 2h, and other is operated with embodiment 1, gets 6,8-dichloro ethyl octylate 45.0g, molar product yield 93.4%, purity 98.1%.
Embodiment 8
Feed intake amount of substance than 6-hydroxyl-8-chloroctanoic acid ethyl ester: two (trichloromethyl) carbonic ether: N, dinethylformamide is 1: 0.4: 1.4,6-hydroxyl-8-chloroctanoic acid ethyl ester charging capacity is 44.5g (200mmol), two (trichloromethyl) carbonic ether charging capacity is 23.74g (80mmol), N, the dinethylformamide charging capacity is 20.44g (280mmol), and the organic solvent of two (trichloromethyl) carbonic ethers of dissolving is a normal hexane, and its consumption is about 2 times of two (trichloromethyl) carbonic ether quality.
Temperature of reaction is 60～65 ℃, and the reaction times is 7h, and other is operated with embodiment 1, gets 6,8-dichloro ethyl octylate 44.3g, molar product yield 91.9%, purity 97.9%.
Embodiment 9
Feed intake amount of substance than 6-hydroxyl-8-chloroctanoic acid ethyl ester: two (trichloromethyl) carbonic ether: N, dinethylformamide is 1: 0.5: 1.5,6-hydroxyl-8-chloroctanoic acid ethyl ester charging capacity is 44.5g (200mmol), two (trichloromethyl) carbonic ether charging capacity is 29.7g (100mmol), N, the dinethylformamide charging capacity is 21.9g (300mmol), and the organic solvent of two (trichloromethyl) carbonic ethers of dissolving is an ethyl acetate, and its consumption is about 1.5 times of two (trichloromethyl) carbonic ether quality.
Temperature of reaction is 55～60 ℃, and the reaction times is 8h, and other is operated with embodiment 1, gets 6,8-dichloro ethyl octylate 43.8g, molar product yield 90.9%, purity 98.0%
Embodiment 10
Feed intake amount of substance than 6-hydroxyl-8-chloroctanoic acid ethyl ester: two (trichloromethyl) carbonic ether: N, dinethylformamide is 1: 0.45: 1.4,6-hydroxyl-8-chloroctanoic acid ethyl ester charging capacity is 44.5g (200mmol), two (trichloromethyl) carbonic ether charging capacity is 26.7g (90mmol), N, the dinethylformamide charging capacity is 20.44g (280mmol), and the organic solvent of two (trichloromethyl) carbonic ethers of dissolving is an ethylene dichloride, and its consumption is about 3 times of two (trichloromethyl) carbonic ether quality.
Temperature of reaction is 75～80 ℃, and the reaction times is 2h, and other is operated with embodiment 1, gets 6,8-dichloro ethyl octylate 44.9g, molar product yield 93.2%, purity 98.4%.
Embodiment 11
Feed intake amount of substance than 6-hydroxyl-8-chloroctanoic acid ethyl ester: two (trichloromethyl) carbonic ether: N, dinethylformamide is 1: 0.34: 1.0,6-hydroxyl-8-chloroctanoic acid ethyl ester charging capacity is 44.5g (200mmol), two (trichloromethyl) carbonic ether charging capacity is 20.2g (68mmol), N, the dinethylformamide charging capacity is 14.6g (200mmol), and the organic solvent of two (trichloromethyl) carbonic ethers of dissolving is a chloroform, and its consumption is about 2.5 times of two (trichloromethyl) carbonic ether quality.
Temperature of reaction is 55～60 ℃, and the reaction times is 7h, and other is operated with embodiment 1, gets 6,8-dichloro ethyl octylate 41.0g, molar product yield 85.1%, purity 97.5%.
Embodiment 12
Feed intake amount of substance than 6-hydroxyl-8-chloroctanoic acid ethyl ester: two (trichloromethyl) carbonic ether: N, dinethylformamide is 1: 1.0: 3.0,6-hydroxyl-8-chloroctanoic acid ethyl ester charging capacity is 44.5g (200mmol), two (trichloromethyl) carbonic ether charging capacity is 59.4g (200mmol), N, the dinethylformamide charging capacity is 43.8g (600mmol), and the organic solvent of two (trichloromethyl) carbonic ethers of dissolving is a toluene, and its consumption is about 2.5 times of two (trichloromethyl) carbonic ether quality.
Temperature of reaction is 75～80 ℃, and the reaction times is 2h, and other is operated with embodiment 1, gets 6,8-dichloro ethyl octylate 41.5g, molar product yield 86.1%, purity 97.8%.
Embodiment 13
Feed intake amount of substance than 6-hydroxyl-8-chloroctanoic acid ethyl ester: two (trichloromethyl) carbonic ether: N, dinethylformamide is 1: 1.0: 1.0,6-hydroxyl-8-chloroctanoic acid ethyl ester charging capacity is 44.5g (200mmol), two (trichloromethyl) carbonic ether charging capacity is 59.4g (200mmol), N, the dinethylformamide charging capacity is 7.3g (100mmol), and the organic solvent of two (trichloromethyl) carbonic ethers of dissolving is a hexanaphthene, and its consumption is about 2 times of two (trichloromethyl) carbonic ether quality.
Temperature of reaction is 65～70 ℃, and the reaction times is 6h, and other is operated with embodiment 1, gets 6,8-dichloro ethyl octylate 31.5g, molar product yield 65.4%, purity 90.8%.
Claims (8)
1. one kind 6, the chemical synthesis process of 8-dichloro ethyl octylate, it is characterized in that described method carries out according to following steps: 6-hydroxyl-8-chloroctanoic acid ethyl ester is dissolved in N, in the dinethylformamide, under agitation drip the solution of the organic solvent that is dissolved with two (trichloromethyl) carbonic ethers under the ice-water bath condition, drip off and slowly be warming up to 50～80 ℃ of reactions 2～8 hours, react the reaction solution that finishes and get 6 through aftertreatment, 8-dichloro ethyl octylate.
2. as claimed in claim 16, the chemical synthesis process of 8-dichloro ethyl octylate, it is characterized in that described 6-hydroxyl-8-chloroctanoic acid ethyl ester: two (trichloromethyl) carbonic ether: N, the amount of substance ratio of dinethylformamide is 1: 0.34～1.0: 1.0～3.0.
3. as claimed in claim 1 or 26, the chemical synthesis process of 8-dichloro ethyl octylate is characterized in that described organic solvent is the mixture of following one or more arbitrary proportions: benzene, toluene, chlorobenzene, normal hexane, hexanaphthene, ethyl acetate, trichloromethane, ethylene dichloride.
4. as claimed in claim 36, the chemical synthesis process of 8-dichloro ethyl octylate, the consumption that it is characterized in that described organic solvent is 1.5～3 times of two (trichloromethyl) carbonic ether quality.
5. as claimed in claim 26, the chemical synthesis process of 8-dichloro ethyl octylate, it is characterized in that described 6-hydroxyl-8-chloroctanoic acid ethyl ester: two (trichloromethyl) carbonic ether: N, the amount of substance ratio of dinethylformamide is 1: 0.34～0.5: 1.0～1.5.
6. as claimed in claim 36, the chemical synthesis process of 8-dichloro ethyl octylate is characterized in that described organic solvent is the mixture of following one or more arbitrary proportions: chlorobenzene, toluene, ethylene dichloride.
7. as claimed in claim 16, the chemical synthesis process of 8-dichloro ethyl octylate, it is characterized in that described aftertreatment is: reaction solution is cooled to be neutralized to neutrality with alkali lye below 30 ℃, and normal pressure boils off solvent, it is described 6 that vacuum distilling gets, 8-dichloro ethyl octylate.
8. as claimed in claim 16, the chemical synthesis process of 8-dichloro ethyl octylate, it is characterized in that described synthetic method carries out according to following steps: according to 6-hydroxyl-8-chloroctanoic acid ethyl ester: two (trichloromethyl) carbonic ether: N, the amount of substance ratio of dinethylformamide is 1: 0.34～0.5: 1.0～1.5 to feed intake, 6-hydroxyl-8-chloroctanoic acid ethyl ester is dissolved in N, in the dinethylformamide, under agitation drip the solution of the organic solvent that is dissolved with two (trichloromethyl) carbonic ethers under the ice-water bath condition, be warmed up to 50～80 ℃ of reactions 2～8 hours after dripping off, reacting the afterreaction liquid that finishes is cooled to below 30 ℃, be neutralized to neutrality with alkali lye, normal pressure boils off solvent, vacuum distilling gets 6,8-dichloro ethyl octylate; Described organic solvent is chlorobenzene or toluene, and the quality of described organic solvent is 1.5～3 times of two (trichloromethyl) carbonic ether quality.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200710156217A CN100593534C (en) | 2007-09-30 | 2007-09-30 | Chemical method for synthesizing 6,8-dichloro ethyl cacodylic acid caprylate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200710156217A CN100593534C (en) | 2007-09-30 | 2007-09-30 | Chemical method for synthesizing 6,8-dichloro ethyl cacodylic acid caprylate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101157614A true CN101157614A (en) | 2008-04-09 |
| CN100593534C CN100593534C (en) | 2010-03-10 |
Family
ID=39305864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200710156217A Active CN100593534C (en) | 2007-09-30 | 2007-09-30 | Chemical method for synthesizing 6,8-dichloro ethyl cacodylic acid caprylate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100593534C (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103232344A (en) * | 2013-04-26 | 2013-08-07 | 南京理工大学 | Method for synthesizing S-2-methyl chloropropionate |
| CN105693510A (en) * | 2016-03-31 | 2016-06-22 | 苏州富士莱医药股份有限公司 | Preparation method of ethyl 6,8-dichlorocaprylate |
| CN106966900A (en) * | 2016-01-13 | 2017-07-21 | 江苏同禾药业有限公司 | A kind of preparation method of 6,8- dicloro caprylates ethyl ester |
| CN106966901A (en) * | 2016-01-13 | 2017-07-21 | 江苏同禾药业有限公司 | A kind of preparation method of 6- hydroxyls -8- Lipase Catalyzed Resolution of Racemic Ethyl |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19533881A1 (en) * | 1995-09-13 | 1997-03-20 | Dresden Arzneimittel | Production and use of the pure enantiomers of 8-chloro-6-sulfonyloxy-octanoic acids and their alkyl esters and of the pure enantiomers of 6,8-dichloro-octanoic acid and their alkyl esters |
| CN1269830C (en) * | 2004-12-22 | 2006-08-16 | 东南大学 | Method for preparing-ester by using solid chlorine substitution of phosgene |
| CN100415702C (en) * | 2006-09-29 | 2008-09-03 | 浙江工业大学 | Synthesis process of 1-chloro octane |
-
2007
- 2007-09-30 CN CN200710156217A patent/CN100593534C/en active Active
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103232344A (en) * | 2013-04-26 | 2013-08-07 | 南京理工大学 | Method for synthesizing S-2-methyl chloropropionate |
| CN103232344B (en) * | 2013-04-26 | 2016-04-20 | 南京理工大学 | A kind of method of synthesizing S-2-methyl chloropropionate |
| CN106966900A (en) * | 2016-01-13 | 2017-07-21 | 江苏同禾药业有限公司 | A kind of preparation method of 6,8- dicloro caprylates ethyl ester |
| CN106966901A (en) * | 2016-01-13 | 2017-07-21 | 江苏同禾药业有限公司 | A kind of preparation method of 6- hydroxyls -8- Lipase Catalyzed Resolution of Racemic Ethyl |
| CN105693510A (en) * | 2016-03-31 | 2016-06-22 | 苏州富士莱医药股份有限公司 | Preparation method of ethyl 6,8-dichlorocaprylate |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100593534C (en) | 2010-03-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105218606B (en) | A kind of method for preparing scutellarin | |
| CN100593534C (en) | Chemical method for synthesizing 6,8-dichloro ethyl cacodylic acid caprylate | |
| CN113004142B (en) | Novel preparation method of 2,4, 5-trifluoro-phenylacetic acid | |
| CN103058989A (en) | Method for preparing alpha-lipoic acid | |
| CN104892666A (en) | Method for preparing high-purity tributyl phosphate | |
| CN104961715A (en) | Preparation method for Dapagliflozin | |
| CN103864615B (en) | A kind of method that continuous on-catalytic method prepares Trifluoroacetic Acid Ethyl Ester | |
| CN102206151B (en) | Synthetic method of royaljelly acid | |
| CN103694094B (en) | A kind of preparation method of the chloro-2 pentanone of 5- | |
| CN102993163A (en) | Synthesis method of 3-methylthiophene-2-aldehyde | |
| CN103896995A (en) | Preparation method of sucralose | |
| CN100549022C (en) | The method for preparing FLUTICASONE PROPIONATE | |
| CN106008183A (en) | Preparation methods for ephedrine or pseudoephedrine and for ephedrine or pseudoephedrine intermediate | |
| CN103113379A (en) | Synthetic process for asenapine maleate | |
| CN104788296B (en) | Preparation method of methyldecane as impurity of colesevelam hydrochloride | |
| CN108395387A (en) | A kind of synthetic method of bromisoval | |
| CN102060826A (en) | Method for synthesizing 7-methoxyl-4'-substituted flavonoids compound | |
| CN101333161B (en) | Method for preparing alpha-chloro-fatty acid | |
| CN111892635A (en) | Novel synthesis method of nicotinamide ribose | |
| CN101045701B (en) | Preparation method of thioacetic acid potassium | |
| CN106674135A (en) | Uracil synthesizing method | |
| CN106565424A (en) | Preparation method for high-purity propofol | |
| CN108383720A (en) | A kind of neighbour's substituted benzoic acid meta position chlorination | |
| CN104761602A (en) | Preparation method of trifluridine | |
| CN108218708B (en) | Preparation method and application of 5-chloro-4-methyl-2-nitrobenzoic acid |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20080409 Assignee: Jiangsu Tonghe Pharmaceutical Co., Ltd. Assignor: Zhejiang University of Technology |Changshu Wanxing Chemical Co., Ltd. Contract record no.: 2010320000394 Denomination of invention: Synthesis process of 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-epoxy ethane Granted publication date: 20100310 License type: Exclusive License Record date: 20100414 |