CN101440020A - Preparation method of (8E,10E) -8, 10-dodecadien-1-ol - Google Patents
Preparation method of (8E,10E) -8, 10-dodecadien-1-ol Download PDFInfo
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- CN101440020A CN101440020A CNA2008102439821A CN200810243982A CN101440020A CN 101440020 A CN101440020 A CN 101440020A CN A2008102439821 A CNA2008102439821 A CN A2008102439821A CN 200810243982 A CN200810243982 A CN 200810243982A CN 101440020 A CN101440020 A CN 101440020A
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- alcohol
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- carbon diene
- preparation
- aftertreatment
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- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- CSWBSLXBXRFNST-MQQKCMAXSA-N (8e,10e)-dodeca-8,10-dien-1-ol Chemical compound C\C=C\C=C\CCCCCCCO CSWBSLXBXRFNST-MQQKCMAXSA-N 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000003944 halohydrins Chemical class 0.000 claims abstract description 9
- 239000007818 Grignard reagent Substances 0.000 claims abstract description 8
- 150000004795 grignard reagents Chemical class 0.000 claims abstract description 7
- 239000005051 trimethylchlorosilane Substances 0.000 claims abstract description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000003747 Grignard reaction Methods 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 43
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 238000004821 distillation Methods 0.000 claims description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 9
- 238000000605 extraction Methods 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 7
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 claims description 7
- 229940094989 trimethylsilane Drugs 0.000 claims description 7
- MCBUWHCCICIHNH-UHFFFAOYSA-N C(CCCCC)O[Si](C)(C)C.[Cl] Chemical compound C(CCCCC)O[Si](C)(C)C.[Cl] MCBUWHCCICIHNH-UHFFFAOYSA-N 0.000 claims description 6
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 6
- 239000012259 ether extract Substances 0.000 claims description 6
- 239000012467 final product Substances 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 5
- 239000013256 coordination polymer Substances 0.000 claims description 5
- 239000012266 salt solution Substances 0.000 claims description 5
- 235000019439 ethyl acetate Nutrition 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- QVFWZNCVPCJQOP-UHFFFAOYSA-N chloralodol Chemical compound CC(O)(C)CC(C)OC(O)C(Cl)(Cl)Cl QVFWZNCVPCJQOP-UHFFFAOYSA-N 0.000 claims description 3
- 229960005083 chloralodol Drugs 0.000 claims description 3
- 239000012153 distilled water Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 230000001681 protective effect Effects 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
- 235000019270 ammonium chloride Nutrition 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 2
- 239000003223 protective agent Substances 0.000 abstract description 2
- DJZFWIANWGTBBQ-UHFFFAOYSA-N 6-chlorohexoxy(trimethyl)silane Chemical compound C[Si](C)(C)OCCCCCCCl DJZFWIANWGTBBQ-UHFFFAOYSA-N 0.000 abstract 2
- HQCIWDKNRBMTSB-BSWSSELBSA-N [(8e,10e)-dodeca-8,10-dienoxy]-trimethylsilane Chemical compound C\C=C\C=C\CCCCCCCO[Si](C)(C)C HQCIWDKNRBMTSB-BSWSSELBSA-N 0.000 abstract 2
- CFDRQRFAQCJPBZ-UHFFFAOYSA-N 1-chlorohexan-1-ol Chemical compound CCCCCC(O)Cl CFDRQRFAQCJPBZ-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 3
- 239000000877 Sex Attractant Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Abstract
The invention discloses a preparation method of (8E,10E) -8, 10-dodecadienol-1-alcohol, which comprises the following steps: reacting chlorohexanol with trimethylchlorosilane under an alkaline condition to obtain chlorohexyloxy trimethylsilane, carrying out Grignard reaction on the chlorohexyloxy trimethylsilane to obtain a Grignard reagent, and carrying out Grignard reaction on Li2CuCl4In the presence of a catalyst, (2E, 4E) -2, 4-hexadiene-1-alcohol acetate and a Grignard reagent are subjected to a coupling reaction to obtain (8E,10E) -8, 10-dodecadiene-1-oxytrimethylsilane, the (8E,10E) -8, 10-dodecadiene-1-oxytrimethylsilane is dissolved in a solution of methanol and water, and p-toluenesulfonic acid is added to react to obtain the (8E,10E) -8, 10-dodecadiene-1-alcohol. The method adopts trimethylchlorosilane as a hydroxyl protective agent of the halohydrin, has low price, is easy to purchase in the market, and can reduce the cost. And the reaction has no stink, the byproduct can be absorbed, the environment is not polluted, the human health is not influenced, and the method is suitable for industrial production.
Description
Technical field
The present invention relates to a kind of preparation method of sex pheromone, particularly relate to a kind of (8E, 10E)-8, the preparation method of 10-12 carbon diene-1-alcohol.
Background technology
The chemical name of carpocapsa pononella sex pheromone is (8E; 10E)-8,10-12 carbon diene-1-alcohol is in the process of synthetic carpocapsa pononella sex pheromone; need protect the hydroxyl of the halohydrin in the raw material, make it in the reaction of back, have stability and structure is not destroyed.
It is with dihydropyrane that the hydroxyl of halohydrin is protected the most frequently used method
As protective material, its reaction equation is:
Wherein X represents halogen.
But, relatively lack on the dihydropyrane market on the one hand, cost an arm and a leg, cause production cost very high.Dihydropyrane also has stench on the other hand, and is easily carcinogenic, and environment, human body are all had bigger harm.So, be difficult to be suitable for suitability for industrialized production.
Summary of the invention
The objective of the invention is to overcome the problems referred to above, provide a kind of cost low, pollute less, little to human body harm, be suitable for suitability for industrialized production (8E, 10E)-8, the preparation method of 10-12 carbon diene-1-alcohol.
The technical scheme that realizes the object of the invention is: a kind of (8E, 10E)-8, the preparation method of 10-12 carbon diene-1-alcohol; preparation (8E; 10E)-8, one of raw material of 10-12 carbon diene-1-alcohol is a halohydrin, and the protective material that the hydroxyl of halohydrin is protected is a trimethylchlorosilane.
Concrete steps are as follows: 1. Mecoral and trimethylchlorosilane are reacted under alkaline condition, the reaction times is 3h～9h, and temperature of reaction is 25 ℃～35 ℃, carries out aftertreatment then and obtains chlorine hexyloxy trimethyl silane.2. the chlorine hexyloxy trimethyl silane through aftertreatment that 1. step is obtained obtains Grignard reagent by grignard reaction.3. at Li
2CuCl
4The existence of catalyzer is down with (2E, 4E)-2, the Grignard reagent that 2. 4-hexadiene-1-alcohol acetic ester and step obtain carries out linked reaction, the temperature of catalyzed reaction is controlled to be-15 ℃～-5 ℃ by icy salt solution, carry out aftertreatment then and obtain (8E, 10E)-8,10-12 carbon diene-1-oxygen base trimethyl silane.4. (the 8E that 3. step is obtained through aftertreatment, 10E)-8,10-12 carbon diene-1-oxygen base trimethyl silane is dissolved in the solution of methyl alcohol and water, add tosic acid and react, sloughed trimethyl silicane in the reaction, the time of reaction is 3h～9h, temperature of reaction is 55 ℃～65 ℃, carry out then aftertreatment obtain (8E, 10E)-8,10-12 carbon diene-1-alcohol finished product.
The alkaline condition of above-mentioned steps described in 1. is for adding Na in reaction soln
2CO
3, make that the pH value of solution is 8～10.
The aftertreatment of above-mentioned steps described in 1. comprises: resultant is added water earlier be hydrolyzed, use ether extraction then, with salt solution and distilled water ether extract is washed to neutrality successively again, use anhydrous Na
2SO
4Carry out drying, remove ether with atmospheric distillation, the fraction of collecting (130～132) ℃/5mmHg with distillation under vacuum gets final product.
The aftertreatment of above-mentioned steps described in 3. comprises: with aqueous ammonium chloride solution resultant is hydrolyzed, uses ether extraction then, wash ether extract again to neutral, use anhydrous Na
2SO
4Drying is removed ether with atmospheric distillation and is got final product.
The aftertreatment of above-mentioned steps described in 4. comprises: under reduced pressure boil off water and methyl alcohol, remainder adds water and is hydrolyzed, and uses ether extraction then, washes ether extract again to neutral, uses anhydrous Na
2SO
4Drying boils off ether with atmospheric distillation, and the fraction of collecting (110～112) ℃/0.2mmHg with distillation under vacuum gets final product.
Described anhydrous Na
2SO
4Be the CP level.
Synthetic route of the present invention is as follows:
Mg is a magnesium chips in the said synthesis route, and THF is a tetrahydrofuran (THF), and TSOH is a tosic acid, and MeOH is a methyl alcohol.Li
2CuCl
4Be to react and make by lithium chloride and cuprous chloride.
The present invention has positive effect: the present invention adopts the hydroxy-protecting agent of trimethylchlorosilane as halohydrin, its low price, and market is purchased easily, can reduce cost; And ordorless during its reaction, by product can absorb, and environmentally safe can not influence HUMAN HEALTH yet, is suitable for suitability for industrialized production.
Embodiment
(embodiment 1)
Present embodiment (8E, 10E)-8, the preparation method of 10-12 carbon diene-1-alcohol has following steps:
1. on the reaction flask of 500mL, thermometer is housed, agitator, moisture eliminator and addition funnel, the Cl (CH of input 100g in reaction flask earlier
2)
6The Na of OH (0.73mo1) and 78g
2CO
3(0.74mol), the pH value of solution is 9, slowly adds (the CH of 103g under the frozen water cooling
3)
3SiCl (0.95mol) adds the back and react 6h under 30 ℃ temperature.Adding 200ml water then is hydrolyzed; With ether extraction three times, merge ether extracted liquid, with salt solution and distilled water ether extracted liquid is washed till neutrality successively again, usefulness CP level anhydrous Na
2SO
4Drying is removed ether solvent with atmospheric distillation, collects the fraction of (130～132) ℃/5mmHg again with distillation under vacuum, obtains the chlorine hexyloxy trimethyl silane of 139.7g, and purity reaches 96%, and yield reaches 92%.
2. in the four-hole bottle of 500mL, drop into the magnesium chips (0.416mol) of 10g, 0.05g iodine grain, the tetrahydrofuran (THF) of 100mL is loaded onto agitator, prolong and thermometer, is heated to the Cl (CH that begins to drip 75.2g after the backflow
2)
6OSi (CH
3)
3(0.36mol) carry out grignard reaction and prepare ClMg (CH
2)
6OSi (CH
3)
3Grignard reagent, 4～6 hours postcooling of back flow reaction are stand-by.
3. in another reaction flask, add the cuprous chloride of 2g lithium chloride and 3g and the tetrahydrofuran (THF) of 100ml earlier and react the Li that obtains 5g
2CuCl
4Catalyzer, add then 35g (2E, 4E)-2, the tetrahydrofuran (THF) of 4-hexadiene-1-alcohol acetic ester (0.25mol) and 100mL is cooled to the Grignard reagent ClMg (CH that 2.-10 ℃ of following agitation and dropping steps prepare with cryosel
2)
6OSi (CH
3)
3, it is more violent to heat up in the reaction, adds in about 2 hours, spends the night in 0 ℃ of left and right sides stirring reaction then.Next day, add the hydrolysis of 300ml saturated ammonium chloride solution; Use ether extraction, wash ether extracted liquid again, with CP level anhydrous Na to neutral
2SO
4Drying is removed ether with atmospheric distillation, obtain 64g (8E, 10E)-8,10-12 carbon diene-1-oxygen base trimethyl silane.
4. in the reaction flask of 1000mL with the 3. (8E of the 64g of gained of step, 10E)-8,10-12 carbon diene-1-oxygen base trimethyl silane (0.25mol) is dissolved in the mixed solvent of 650mL methyl alcohol and 70mL water, adds tosic acid 16g, is heated to 60 ℃ with heating jacket under stirring and reacts, reaction times is 6h, under reduced pressure boil off water and methyl alcohol again, remainder adds 200ml water and is hydrolyzed, and uses ether extraction, wash ether extracted liquid again to neutral, with CP level anhydrous Na
2SO
4Drying boils off ether with atmospheric distillation, collects the fraction of (110～112) ℃/0.2mmHg in the presence of vacuum pump with distillation under vacuum, product (8E, 10E)-8,10-12 carbon diene-1-alcohol 27.3g (0.15mol), yield 60%, product purity 95.6%.
(embodiment 2～embodiment 5)
The preparation method of each embodiment is substantially the same manner as Example 1, and difference sees Table 1.
Table 1
In the table 1: raw material A be (2E, 4E)-2,4-hexadiene-1-alcohol acetic ester.Product A is a chlorine hexyloxy trimethyl silane.Product B be (8E, 10E)-8,10-12 carbon diene-1-oxygen base trimethyl silane.Product C be (8E, 10E)-8,10-12 carbon diene-1-alcohol.
Claims (7)
1, a kind of (8E, 10E)-8, the preparation method of 10-12 carbon diene-1-alcohol, the preparation (8E, 10E)-8, one of raw material of 10-12 carbon diene-1-alcohol is a halohydrin; It is characterized in that: the protective material that the hydroxyl of halohydrin is protected is a trimethylchlorosilane.
2, according to claim 1 (8E, 10E)-8, the preparation method of 10-12 carbon diene-1-alcohol, it is characterized in that: halohydrin is a Mecoral, has following steps:
1. Mecoral and trimethylchlorosilane are reacted under alkaline condition, the reaction times is 3h～9h, and temperature of reaction is 25 ℃～35 ℃, carries out aftertreatment then and obtains chlorine hexyloxy trimethyl silane;
2. the chlorine hexyloxy trimethyl silane through aftertreatment that 1. step is obtained obtains Grignard reagent by grignard reaction;
3. at Li
2CuCl
4The existence of catalyzer is down with (2E, 4E)-2, the Grignard reagent that 2. 4-hexadiene-1-alcohol acetic ester and step obtain carries out linked reaction, the temperature of catalyzed reaction is controlled to be-15 ℃～-5 ℃ by icy salt solution, carry out aftertreatment then and obtain (8E, 10E)-8,10-12 carbon diene-1-oxygen base trimethyl silane;
4. (the 8E that 3. step is obtained through aftertreatment, 10E)-8,10-12 carbon diene-1-oxygen base trimethyl silane is dissolved in the solution of methyl alcohol and water, add tosic acid and react, sloughed trimethyl silicane in the reaction, the time of reaction is 3h～9h, temperature of reaction is 55 ℃～65 ℃, carry out then aftertreatment obtain (8E, 10E)-8,10-12 carbon diene-1-alcohol finished product.
It is 3, according to claim 2 that (8E, 10E)-8, the preparation method of 10-12 carbon diene-1-alcohol is characterized in that: the alkaline condition of step described in 1. is for adding Na in reaction soln
2CO
3, make that the pH value of solution is 8～10.
4, (8E according to claim 2,10E)-8, the preparation method of 10-12 carbon diene-1-alcohol, it is characterized in that: the aftertreatment of step described in 1. comprises: resultant is added water earlier be hydrolyzed, use ether extraction then, with salt solution and distilled water ether extract is washed to neutrality successively again, uses anhydrous Na
2SO
4Carry out drying, remove ether with atmospheric distillation, the fraction of collecting (130～132) ℃/5mmHg with distillation under vacuum gets final product.
5, according to claim 2 (8E, 10E)-8, the preparation method of 10-12 carbon diene-1-alcohol, it is characterized in that: the aftertreatment of step described in 3. comprises: with aqueous ammonium chloride solution resultant is hydrolyzed, use ether extraction then, wash ether extract again, use anhydrous Na to neutral
2SO
4Drying is removed ether with atmospheric distillation and is got final product.
6, (8E according to claim 2,10E)-8, the preparation method of 10-12 carbon diene-1-alcohol, it is characterized in that: the aftertreatment of step described in 4. comprises: under reduced pressure boil off water and methyl alcohol, remainder adds water and is hydrolyzed, use ether extraction then, wash ether extract again, use anhydrous Na to neutral
2SO
4Drying boils off ether with atmospheric distillation, and the fraction of collecting (110～112) ℃/0.2mmHg with distillation under vacuum gets final product.
7, described (8E, 10E)-8, the preparation method of 10-12 carbon diene-1-alcohol is characterized in that: described anhydrous Na according to one of claim 4 to 6
2SO
4Be the CP level.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008102439821A CN101440020A (en) | 2008-12-19 | 2008-12-19 | Preparation method of (8E,10E) -8, 10-dodecadien-1-ol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008102439821A CN101440020A (en) | 2008-12-19 | 2008-12-19 | Preparation method of (8E,10E) -8, 10-dodecadien-1-ol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101440020A true CN101440020A (en) | 2009-05-27 |
Family
ID=40724652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2008102439821A Pending CN101440020A (en) | 2008-12-19 | 2008-12-19 | Preparation method of (8E,10E) -8, 10-dodecadien-1-ol |
Country Status (1)
| Country | Link |
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| CN (1) | CN101440020A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102718631A (en) * | 2012-07-12 | 2012-10-10 | 常州胜杰化工有限公司 | Preparation method of (8E, 10E)-8, 10-dodecadienol-1-alcohol |
| CN107056610A (en) * | 2017-06-14 | 2017-08-18 | 黑龙江省科学院微生物研究所 | The synthetic method of sex pheromones of Spodoptera litura Fabricius |
| CN109467504A (en) * | 2017-09-07 | 2019-03-15 | 信越化学工业株式会社 | The method for preparing (4Z, 7Z) -4,7- decadinene -1- yl acetate |
| CN110078593A (en) * | 2018-11-15 | 2019-08-02 | 南通正达农化有限公司 | A kind of synthetic method of sex pheromone of carpocapsa pomonella |
| CN115304463A (en) * | 2022-08-11 | 2022-11-08 | 中国农业科学院植物保护研究所 | Preparation method of codling moth pheromone |
-
2008
- 2008-12-19 CN CNA2008102439821A patent/CN101440020A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102718631A (en) * | 2012-07-12 | 2012-10-10 | 常州胜杰化工有限公司 | Preparation method of (8E, 10E)-8, 10-dodecadienol-1-alcohol |
| CN102718631B (en) * | 2012-07-12 | 2016-08-24 | 常州胜杰化工有限公司 | The preparation method of (8E, 10E)-8,10-12 carbon diene-1-alcohol |
| CN107056610A (en) * | 2017-06-14 | 2017-08-18 | 黑龙江省科学院微生物研究所 | The synthetic method of sex pheromones of Spodoptera litura Fabricius |
| CN109467504A (en) * | 2017-09-07 | 2019-03-15 | 信越化学工业株式会社 | The method for preparing (4Z, 7Z) -4,7- decadinene -1- yl acetate |
| CN109467504B (en) * | 2017-09-07 | 2022-04-08 | 信越化学工业株式会社 | Process for preparing (4Z,7Z) -4, 7-decadien-1-yl acetate |
| CN110078593A (en) * | 2018-11-15 | 2019-08-02 | 南通正达农化有限公司 | A kind of synthetic method of sex pheromone of carpocapsa pomonella |
| CN115304463A (en) * | 2022-08-11 | 2022-11-08 | 中国农业科学院植物保护研究所 | Preparation method of codling moth pheromone |
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Application publication date: 20090527 |