JPS6366813B2 - - Google Patents
Info
- Publication number
- JPS6366813B2 JPS6366813B2 JP55048935A JP4893580A JPS6366813B2 JP S6366813 B2 JPS6366813 B2 JP S6366813B2 JP 55048935 A JP55048935 A JP 55048935A JP 4893580 A JP4893580 A JP 4893580A JP S6366813 B2 JPS6366813 B2 JP S6366813B2
- Authority
- JP
- Japan
- Prior art keywords
- cis
- chloride
- reaction
- nonene
- tetrahydrofuran
- 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.)
- Expired
Links
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
- 239000007818 Grignard reagent Substances 0.000 claims description 5
- KSOUCCXMYMQGDF-UHFFFAOYSA-L dichlorocopper;lithium Chemical compound [Li].Cl[Cu]Cl KSOUCCXMYMQGDF-UHFFFAOYSA-L 0.000 claims description 5
- 150000004795 grignard reagents Chemical class 0.000 claims description 5
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 claims description 4
- UGKKOFVRPCHOHR-UHFFFAOYSA-J [Cu](Cl)(Cl)(Cl)Cl.[Li].[Li] Chemical compound [Cu](Cl)(Cl)(Cl)Cl.[Li].[Li] UGKKOFVRPCHOHR-UHFFFAOYSA-J 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 description 4
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 4
- 239000000877 Sex Attractant Substances 0.000 description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XJHRZBIBSSVCEL-ARJAWSKDSA-N (Z)-non-6-en-1-ol Chemical compound CC\C=C/CCCCCO XJHRZBIBSSVCEL-ARJAWSKDSA-N 0.000 description 2
- RTNPCOBSXBGDMO-ARJAWSKDSA-N (Z)-non-6-enal Chemical compound CC\C=C/CCCCC=O RTNPCOBSXBGDMO-ARJAWSKDSA-N 0.000 description 2
- XJHRZBIBSSVCEL-UHFFFAOYSA-N Z-Non-6-en-1-ol Natural products CCC=CCCCCCO XJHRZBIBSSVCEL-UHFFFAOYSA-N 0.000 description 2
- 235000021028 berry Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000006880 cross-coupling reaction Methods 0.000 description 2
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- YJINQJFQLQIYHX-PLNGDYQASA-N 11Z-Tetradecenyl acetate Chemical compound CC\C=C/CCCCCCCCCCOC(C)=O YJINQJFQLQIYHX-PLNGDYQASA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- MFFQOUCMBNXSBK-PLNGDYQASA-N 9Z-Dodecenyl acetate Chemical compound CC\C=C/CCCCCCCCOC(C)=O MFFQOUCMBNXSBK-PLNGDYQASA-N 0.000 description 1
- IOUUIFSIQMVYKP-UHFFFAOYSA-N Tetradecanoyl acetate Natural products CCCCCCCCCCCCCCOC(C)=O IOUUIFSIQMVYKP-UHFFFAOYSA-N 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- MAAMIILYYYQTQW-OUKQBFOZSA-N [(e)-dodec-1-enyl] acetate Chemical compound CCCCCCCCCC\C=C\OC(C)=O MAAMIILYYYQTQW-OUKQBFOZSA-N 0.000 description 1
- UECPLNNAVLEZGO-CCEZHUSRSA-N [(e)-tetradec-1-enyl] acetate Chemical compound CCCCCCCCCCCC\C=C\OC(C)=O UECPLNNAVLEZGO-CCEZHUSRSA-N 0.000 description 1
- DFRXMRZQBMFKMI-PLNGDYQASA-N [(z)-non-6-enyl] acetate Chemical group CC\C=C/CCCCCOC(C)=O DFRXMRZQBMFKMI-PLNGDYQASA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YJINQJFQLQIYHX-UHFFFAOYSA-N trans-11-tetradecenyl acetate Natural products CCC=CCCCCCCCCCCOC(C)=O YJINQJFQLQIYHX-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/2632—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving an organo-magnesium compound, e.g. Grignard synthesis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4893580A JPS56145232A (en) | 1980-04-14 | 1980-04-14 | Preparation of cis-6-nonene-1-chloride |
US06/253,061 US4355193A (en) | 1980-04-14 | 1981-04-10 | Method for the preparation of cis-nonen-6-yl chloride |
DE8181102781T DE3162744D1 (en) | 1980-04-14 | 1981-04-10 | Method for the preparation of cis-nonen-6-yl chloride |
EP81102781A EP0038053B1 (en) | 1980-04-14 | 1981-04-10 | Method for the preparation of cis-nonen-6-yl chloride |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4893580A JPS56145232A (en) | 1980-04-14 | 1980-04-14 | Preparation of cis-6-nonene-1-chloride |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS56145232A JPS56145232A (en) | 1981-11-11 |
JPS6366813B2 true JPS6366813B2 (US06168776-20010102-C00028.png) | 1988-12-22 |
Family
ID=12817112
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP4893580A Granted JPS56145232A (en) | 1980-04-14 | 1980-04-14 | Preparation of cis-6-nonene-1-chloride |
Country Status (4)
Country | Link |
---|---|
US (1) | US4355193A (US06168776-20010102-C00028.png) |
EP (1) | EP0038053B1 (US06168776-20010102-C00028.png) |
JP (1) | JPS56145232A (US06168776-20010102-C00028.png) |
DE (1) | DE3162744D1 (US06168776-20010102-C00028.png) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7932410B2 (en) * | 2008-10-31 | 2011-04-26 | Bedoukian Research, Inc. | Production of pheromones and fragrances from substituted and unsubstituted 1-alken-3yl alkylates |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB859897A (en) * | 1958-07-05 | 1961-01-25 | Roche Products Ltd | Novel unsaturated acids and esters thereof and a process for the manufacture and conversion of same |
US3825607A (en) * | 1972-01-17 | 1974-07-23 | Zoecon Corp | Synthesis of 1-bromo-trans-3,trans-5-heptadiene |
-
1980
- 1980-04-14 JP JP4893580A patent/JPS56145232A/ja active Granted
-
1981
- 1981-04-10 DE DE8181102781T patent/DE3162744D1/de not_active Expired
- 1981-04-10 US US06/253,061 patent/US4355193A/en not_active Expired - Lifetime
- 1981-04-10 EP EP81102781A patent/EP0038053B1/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
US4355193A (en) | 1982-10-19 |
EP0038053A1 (en) | 1981-10-21 |
JPS56145232A (en) | 1981-11-11 |
DE3162744D1 (en) | 1984-04-26 |
EP0038053B1 (en) | 1984-03-21 |
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