JPS6254288B2 - - Google Patents
Info
- Publication number
- JPS6254288B2 JPS6254288B2 JP6972480A JP6972480A JPS6254288B2 JP S6254288 B2 JPS6254288 B2 JP S6254288B2 JP 6972480 A JP6972480 A JP 6972480A JP 6972480 A JP6972480 A JP 6972480A JP S6254288 B2 JPS6254288 B2 JP S6254288B2
- Authority
- JP
- Japan
- Prior art keywords
- cis
- grignard reagent
- general formula
- formula
- halo
- 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
- 239000007818 Grignard reagent Substances 0.000 claims description 11
- 150000004795 grignard reagents Chemical class 0.000 claims description 11
- -1 copper halide Chemical class 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 125000006416 CBr Chemical group BrC* 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 239000000877 Sex Attractant Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 5
- BXJHOKLLMOYSRQ-QOXWLJPHSA-N [(7z,11z)-hexadeca-7,11-dienyl] acetate Chemical compound CCCC\C=C/CC\C=C/CCCCCCOC(C)=O BXJHOKLLMOYSRQ-QOXWLJPHSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 3
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- SUCYDSJQVVGOIW-WAYWQWQTSA-N 8Z-Dodecenyl acetate Chemical compound CCC\C=C/CCCCCCCOC(C)=O SUCYDSJQVVGOIW-WAYWQWQTSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 241000218691 Cupressaceae Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- XXPBOEBNDHAAQH-UHFFFAOYSA-N (Z)-12-Tetradecenyl acetate Natural products CCCCC=CCCCCCCCCOC(C)=O XXPBOEBNDHAAQH-UHFFFAOYSA-N 0.000 description 1
- BDOOYDRTBWAVQH-UHFFFAOYSA-N 1,6-dibromohex-1-yne Chemical compound BrCCCCC#CBr BDOOYDRTBWAVQH-UHFFFAOYSA-N 0.000 description 1
- SPNMFERZTLVHJE-UHFFFAOYSA-N 1,8-dibromooct-1-yne Chemical compound BrCCCCCCC#CBr SPNMFERZTLVHJE-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- XXPBOEBNDHAAQH-SREVYHEPSA-N 9Z-Tetradecenyl acetate Chemical compound CCCC\C=C/CCCCCCCCOC(C)=O XXPBOEBNDHAAQH-SREVYHEPSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 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
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000011981 lindlar catalyst Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- ZKUUVVYMPUDTGJ-UHFFFAOYSA-N methyl 5-hydroxy-4-methoxy-2-nitrobenzoate Chemical compound COC(=O)C1=CC(O)=C(OC)C=C1[N+]([O-])=O ZKUUVVYMPUDTGJ-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- ORQYPOUSZINNCB-UHFFFAOYSA-N potassium;hypobromite Chemical compound [K+].Br[O-] ORQYPOUSZINNCB-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6972480A JPS56166130A (en) | 1980-05-26 | 1980-05-26 | Preparation of alkynyl halide compound |
| DE8181103926T DE3165969D1 (en) | 1980-05-26 | 1981-05-21 | Alkynyl halide compounds and alkenyl acetate compounds therefrom |
| EP81103926A EP0040829B1 (en) | 1980-05-26 | 1981-05-21 | Alkynyl halide compounds and alkenyl acetate compounds therefrom |
| US06/266,614 US4391984A (en) | 1980-05-26 | 1981-05-22 | Alkynyl halide compounds and alkenyl acetate compounds therefrom |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6972480A JPS56166130A (en) | 1980-05-26 | 1980-05-26 | Preparation of alkynyl halide compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56166130A JPS56166130A (en) | 1981-12-21 |
| JPS6254288B2 true JPS6254288B2 (bg) | 1987-11-13 |
Family
ID=13411065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6972480A Granted JPS56166130A (en) | 1980-05-26 | 1980-05-26 | Preparation of alkynyl halide compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56166130A (bg) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58128330A (ja) * | 1982-01-26 | 1983-07-30 | Shin Etsu Chem Co Ltd | ５−クロロ−１−ブロモ−１−ペンチン |
-
1980
- 1980-05-26 JP JP6972480A patent/JPS56166130A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56166130A (en) | 1981-12-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Lautens et al. | A Route to the Preparation of γ-Hydroxyvinylstannanes | |
| JP2618221B2 (ja) | 殺虫剤製造用中間体 | |
| JP2528972B2 (ja) | アルキニル化合物の連続製造方法 | |
| 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 | |
| JPS6254288B2 (bg) | ||
| JP5898425B2 (ja) | クラウンエーテル様環状構造及びビナフチル基を有する新規化合物及びその製造方法 | |
| JPS6212770B2 (bg) | ||
| JP2827050B2 (ja) | ４―ｔｅｒｔ―ブトキシ―４′―フルオロビフェニルおよびその製造法 | |
| JP3905340B2 (ja) | 有機金属化合物の新規調製法 | |
| JPH0717660B2 (ja) | １，１―ジクロロ―１，２，２―トリメチル―２―フェニルジシランの製造方法 | |
| JP2000086675A (ja) | シランの製造法 | |
| JPH07330786A (ja) | 光学活性３級ホスフィン化合物、これを配位子とする遷移金属錯体およびこれを用いる製造法 | |
| JP2000080082A (ja) | ５−ハロゲノ−２−置換ピリジンの製造方法 | |
| JP3477631B2 (ja) | １，３−ビス（３−アミノプロピル）−１，１，３，３−テトラオルガノジシロキサンの精製方法 | |
| EP0040829A2 (en) | Alkynyl halide compounds and alkenyl acetate compounds therefrom | |
| 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 | |
| JPH0748387A (ja) | ｔｅｒｔ−ブチルジアルコキシシラン及びその製造方法 | |
| JP4243397B2 (ja) | 新規な不飽和２級アルコールおよびその製造法 | |
| JP3457022B2 (ja) | シリルエステルとエポキシドの付加物及びその製造方法 | |
| JP2838193B2 (ja) | 環状シリルエノールエーテルの製法 | |
| JP4800933B2 (ja) | シクロプロパンモノアセタール誘導体の製造方法およびその中間体 | |
| JP2023077768A (ja) | ３，７－ジメチルアルカン化合物の製造方法 | |
| JPH05255353A (ja) | 光学活性アリル（フルオロ）シランおよびその製造方法 | |
| JPS607616B2 (ja) | α，α―ジ置換酢酸エステルおよびその製造法 | |
| JPS6039080B2 (ja) | 有機ケイ素化合物の製造方法 |