JPH0114886B2 - - Google Patents
Info
- Publication number
- JPH0114886B2 JPH0114886B2 JP15665486A JP15665486A JPH0114886B2 JP H0114886 B2 JPH0114886 B2 JP H0114886B2 JP 15665486 A JP15665486 A JP 15665486A JP 15665486 A JP15665486 A JP 15665486A JP H0114886 B2 JPH0114886 B2 JP H0114886B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- methylpentadecane
- grignard reagent
- octadecene
- 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
- 125000005843 halogen group Chemical group 0.000 claims description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- NAEZQVWAWSVOSD-UHFFFAOYSA-N -14-Methyl-1-octadecene Natural products CCCCC(C)CCCCCCCCCCCC=C NAEZQVWAWSVOSD-UHFFFAOYSA-N 0.000 description 14
- 239000007818 Grignard reagent Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 150000004795 grignard reagents Chemical class 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- VZRJTATVCQVKGL-UHFFFAOYSA-N CCCCC(C)CCCCCCCCCCCl Chemical compound CCCCC(C)CCCCCCCCCCCl VZRJTATVCQVKGL-UHFFFAOYSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 4
- 239000000877 Sex Attractant Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 4
- HANVOGLDKHFHBY-UHFFFAOYSA-N nonadec-2-ene Chemical compound CCCCCCCCCCCCCCCCC=CC HANVOGLDKHFHBY-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- KWUXQDMJRRVZKL-UHFFFAOYSA-N 1-bromo-11-methylpentadecane Chemical compound CCCCC(C)CCCCCCCCCCBr KWUXQDMJRRVZKL-UHFFFAOYSA-N 0.000 description 3
- 244000144730 Amygdalus persica Species 0.000 description 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 235000006040 Prunus persica var persica Nutrition 0.000 description 3
- UGKKOFVRPCHOHR-UHFFFAOYSA-J [Cu](Cl)(Cl)(Cl)Cl.[Li].[Li] Chemical compound [Cu](Cl)(Cl)(Cl)Cl.[Li].[Li] UGKKOFVRPCHOHR-UHFFFAOYSA-J 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- -1 copper halide Chemical class 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 2
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GTQHJCOHNAFHRE-UHFFFAOYSA-N 1,10-dibromodecane Chemical compound BrCCCCCCCCCCBr GTQHJCOHNAFHRE-UHFFFAOYSA-N 0.000 description 1
- AMJBCNIDVLQCBR-UHFFFAOYSA-N 1-bromo-10-chlorodecane Chemical compound ClCCCCCCCCCCBr AMJBCNIDVLQCBR-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- GLCIPJOIEVLTPR-UHFFFAOYSA-N 2-chlorohexane Chemical compound CCCCC(C)Cl GLCIPJOIEVLTPR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001414720 Cicadellidae Species 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 241001190211 Lyonetia Species 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- CPELXLSAUQHCOX-OUBTZVSYSA-N bromine-81 Chemical compound [81BrH] CPELXLSAUQHCOX-OUBTZVSYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical group I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000004809 thin layer chromatography 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
- 229920002554 vinyl polymer Polymers 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15665486A JPS6314741A (ja) | 1986-07-03 | 1986-07-03 | １−ハロ−１１−メチルペンタデカン |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15665486A JPS6314741A (ja) | 1986-07-03 | 1986-07-03 | １−ハロ−１１−メチルペンタデカン |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6314741A JPS6314741A (ja) | 1988-01-21 |
| JPH0114886B2 true JPH0114886B2 (zh) | 1989-03-14 |
Family
ID=15632377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15665486A Granted JPS6314741A (ja) | 1986-07-03 | 1986-07-03 | １−ハロ−１１−メチルペンタデカン |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6314741A (zh) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111440046B (zh) * | 2020-03-05 | 2022-09-16 | 塔里木大学 | 一种鳞翅目害虫桃潜叶蛾性信息素(s)-14-甲基-1-十八碳烯的合成方法 |
-
1986
- 1986-07-03 JP JP15665486A patent/JPS6314741A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6314741A (ja) | 1988-01-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6145617B2 (zh) | ||
| JP3356495B2 (ja) | １−ハロ−シス−３−テトラデセンおよびこれを用いるシス−オレフィン化合物の製造方法 | |
| JP2693615B2 (ja) | １‐ハロ‐４，６，１０‐ヘキサデカトリエン化合物およびその製造方法 | |
| EP0032396A1 (en) | Cis-6-undecene-1-chloride and a method for the preparation thereof | |
| JPH0114886B2 (zh) | ||
| JP3200099B2 (ja) | パーフルオロアルキルトリメチルシランの製造法 | |
| Kruglaya et al. | Silyl-and germylmercurials in organic synthesis. A new route to O-silylated and O-germylated enolates | |
| JP2502936B2 (ja) | 新規なアセチレン系誘導体 | |
| JP3128192B2 (ja) | アリルトリアルコキシシラン化合物の製造方法 | |
| JPH0627084B2 (ja) | ポリフルオロエノラ−トの製造法 | |
| JPH10130178A (ja) | ｇｅｍ−ジフルオロオレフィン類の製造方法、同製造方法に用いるジルコノセン、及びその製造方法 | |
| JP2632638B2 (ja) | ４−フェニルブタノールの製造法 | |
| JPS6254287B2 (zh) | ||
| JP3634874B2 (ja) | トリフルオロメチルアセチレン誘導体、その製造方法およびその中間体の製造方法 | |
| JPH10101614A (ja) | α，α−ジフルオロ−β−ヒドロキシエステルの製造方法 | |
| JPH0546345B2 (zh) | ||
| JP2765575B2 (ja) | 置換シクロペンテノン及び置換シクロヘキセノン誘導体の製造法 | |
| JP3056360B2 (ja) | γ−コロナールの製法 | |
| JPH01249736A (ja) | アルコールの製造方法 | |
| JPH05339277A (ja) | ジシクロアルキルジアルコキシシランの製造方法 | |
| JPH0586770B2 (zh) | ||
| JPS634814B2 (zh) | ||
| JPS642110B2 (zh) | ||
| JPS60188340A (ja) | ２，３−ジメチルペンタナ−ルの製造方法 | |
| WO2002050009A1 (en) | Process for the synthesis of 1-(3,5-bis(trifluoromethyl)-phenyl)ethan-1-one |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |