CS244686B2 - Preparation method of nonane or nonne - Google Patents
Preparation method of nonane or nonne Download PDFInfo
- Publication number
- CS244686B2 CS244686B2 CS841012A CS101284A CS244686B2 CS 244686 B2 CS244686 B2 CS 244686B2 CS 841012 A CS841012 A CS 841012A CS 101284 A CS101284 A CS 101284A CS 244686 B2 CS244686 B2 CS 244686B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- methanol
- isopropylphenyl
- solution
- methoxy
- dimethyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 title claims description 13
- 241001314285 Lymantria monacha Species 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 30
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000002904 solvent Substances 0.000 claims abstract description 22
- 239000000376 reactant Substances 0.000 claims abstract description 16
- CYAKWEQUWJAHLW-UHFFFAOYSA-N 1-(chloromethyl)-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(CCl)C=C1 CYAKWEQUWJAHLW-UHFFFAOYSA-N 0.000 claims abstract description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims abstract description 12
- YEWDJWBVWLXKNY-UHFFFAOYSA-M triphenyl-[(4-propan-2-ylphenyl)methyl]phosphanium;chloride Chemical compound [Cl-].C1=CC(C(C)C)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 YEWDJWBVWLXKNY-UHFFFAOYSA-M 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 108
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- OQBDTGXHFCOCEP-UHFFFAOYSA-N 1-(8-methoxy-4,8-dimethylnon-1-enyl)-4-propan-2-ylbenzene Chemical compound COC(C)(C)CCCC(C)CC=CC1=CC=C(C(C)C)C=C1 OQBDTGXHFCOCEP-UHFFFAOYSA-N 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical class CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 3
- LTNBHNLTEGZRFB-UHFFFAOYSA-N 1-(8-methoxy-4,8-dimethylnonyl)-4-propan-2-ylbenzene Chemical compound COC(C)(C)CCCC(C)CCCC1=CC=C(C(C)C)C=C1 LTNBHNLTEGZRFB-UHFFFAOYSA-N 0.000 abstract description 8
- OQBDTGXHFCOCEP-YRNVUSSQSA-N 1-[(e)-8-methoxy-4,8-dimethylnon-1-enyl]-4-propan-2-ylbenzene Chemical compound COC(C)(C)CCCC(C)C\C=C\C1=CC=C(C(C)C)C=C1 OQBDTGXHFCOCEP-YRNVUSSQSA-N 0.000 abstract description 3
- IDWULKZGRNHZNR-UHFFFAOYSA-N 7-methoxy-3,7-dimethyloctanal Chemical compound COC(C)(C)CCCC(C)CC=O IDWULKZGRNHZNR-UHFFFAOYSA-N 0.000 abstract description 2
- 239000013067 intermediate product Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 description 20
- 238000010992 reflux Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 241000257303 Hymenoptera Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 238000005191 phase separation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- -1 -isopropyl triphenylphosphonium chloride Chemical compound 0.000 description 2
- NQMUGNMMFTYOHK-UHFFFAOYSA-N 1-methoxynaphthalene Chemical compound C1=CC=C2C(OC)=CC=CC2=C1 NQMUGNMMFTYOHK-UHFFFAOYSA-N 0.000 description 2
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 241000238876 Acari Species 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- REJGOFYVRVIODZ-UHFFFAOYSA-N phosphanium;chloride Chemical compound P.Cl REJGOFYVRVIODZ-UHFFFAOYSA-N 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 241000517830 Solenopsis geminata Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000009313 farming Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960001679 octinoxate Drugs 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- AVCVDUDESCZFHJ-UHFFFAOYSA-N triphenylphosphane;hydrochloride Chemical compound [Cl-].C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 AVCVDUDESCZFHJ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5456—Arylalkanephosphonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/465,943 US4482751A (en) | 1983-02-14 | 1983-02-14 | Method for preparation of 8-methoxy-4,8-dimethyl-1-(4-isopropylphenyl)-nonane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS244686B2 true CS244686B2 (en) | 1986-08-14 |
Family
ID=23849805
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS841012A CS244686B2 (en) | 1983-02-14 | 1984-02-13 | Preparation method of nonane or nonne |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4482751A (xx) |
| EP (1) | EP0116370B1 (xx) |
| JP (1) | JPS59155335A (xx) |
| KR (1) | KR840007553A (xx) |
| AU (1) | AU565427B2 (xx) |
| BR (1) | BR8400617A (xx) |
| CA (1) | CA1220789A (xx) |
| CS (1) | CS244686B2 (xx) |
| DD (2) | DD228242A5 (xx) |
| DE (1) | DE3460313D1 (xx) |
| GT (1) | GT198400017A (xx) |
| HU (1) | HU195468B (xx) |
| IL (1) | IL70932A (xx) |
| MX (1) | MX159452A (xx) |
| NZ (1) | NZ207123A (xx) |
| RO (1) | RO88542A (xx) |
| SU (1) | SU1407396A3 (xx) |
| ZA (1) | ZA841021B (xx) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3467307B2 (ja) * | 1994-03-31 | 2003-11-17 | 信越化学工業株式会社 | ホスホニウム塩の製造方法 |
| RU2533831C1 (ru) * | 2013-08-21 | 2014-11-20 | Федеральное государственное бюджетное учреждение науки Институт элементоорганических соединений им. А.Н. Несмеянова Российской академии наук (ИНЭОС РАН) | Способ получения 1-(8-метокси-4,8-диметилнонил)-4-(1-метилэтил)бензола (варианты) |
| RU2561272C1 (ru) * | 2014-08-18 | 2015-08-27 | Федеральное государственное бюджетное учреждение науки Институт элементоорганических соединений им. А.Н. Несмеянова Российской академии наук (ИНЭОС РАН) | Способ получения 1-(8-метокси-4,8-диметилнонил)-4-(1-метилэтил)бензола из изопрена (варианты) |
| US20240002400A1 (en) * | 2020-11-25 | 2024-01-04 | Amgen Inc. | Enantioselective alkenylation of aldehydes |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2703814A (en) * | 1952-03-26 | 1955-03-08 | Monsanto Chemicals | Process of preparing organic phosphorus compounds |
| US4002769A (en) * | 1974-08-16 | 1977-01-11 | The United States Of America As Represented By The Secretary Of Agriculture | Insect maturation inhibitors |
-
1983
- 1983-02-14 US US06/465,943 patent/US4482751A/en not_active Expired - Fee Related
-
1984
- 1984-02-07 DE DE8484101248T patent/DE3460313D1/de not_active Expired
- 1984-02-07 EP EP84101248A patent/EP0116370B1/en not_active Expired
- 1984-02-10 CA CA000447198A patent/CA1220789A/en not_active Expired
- 1984-02-13 NZ NZ207123A patent/NZ207123A/en unknown
- 1984-02-13 SU SU843707404A patent/SU1407396A3/ru active
- 1984-02-13 BR BR8400617A patent/BR8400617A/pt unknown
- 1984-02-13 IL IL70932A patent/IL70932A/xx not_active IP Right Cessation
- 1984-02-13 AU AU24524/84A patent/AU565427B2/en not_active Ceased
- 1984-02-13 RO RO84113581A patent/RO88542A/ro unknown
- 1984-02-13 DD DD84275795A patent/DD228242A5/de not_active IP Right Cessation
- 1984-02-13 KR KR1019840000674A patent/KR840007553A/ko not_active IP Right Cessation
- 1984-02-13 HU HU84561A patent/HU195468B/hu not_active IP Right Cessation
- 1984-02-13 DD DD84260053A patent/DD223438A5/de not_active IP Right Cessation
- 1984-02-13 CS CS841012A patent/CS244686B2/cs unknown
- 1984-02-13 ZA ZA841021A patent/ZA841021B/xx unknown
- 1984-02-13 GT GT198400017A patent/GT198400017A/es unknown
- 1984-02-13 JP JP59023024A patent/JPS59155335A/ja active Granted
- 1984-02-14 MX MX200325A patent/MX159452A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX159452A (es) | 1989-06-09 |
| SU1407396A3 (ru) | 1988-06-30 |
| DD228242A5 (de) | 1985-10-09 |
| RO88542A (ro) | 1986-02-28 |
| KR840007553A (ko) | 1984-12-08 |
| US4482751A (en) | 1984-11-13 |
| AU565427B2 (en) | 1987-09-17 |
| IL70932A0 (en) | 1984-05-31 |
| DD223438A5 (de) | 1985-06-12 |
| EP0116370A1 (en) | 1984-08-22 |
| ZA841021B (en) | 1985-01-30 |
| EP0116370B1 (en) | 1986-07-23 |
| HU195468B (en) | 1988-05-30 |
| JPS59155335A (ja) | 1984-09-04 |
| AU2452484A (en) | 1984-08-23 |
| BR8400617A (pt) | 1984-09-18 |
| CA1220789A (en) | 1987-04-21 |
| GT198400017A (es) | 1985-08-06 |
| DE3460313D1 (en) | 1986-08-28 |
| IL70932A (en) | 1986-12-31 |
| NZ207123A (en) | 1987-04-30 |
| HUT34718A (en) | 1985-04-28 |
| JPH0237901B2 (xx) | 1990-08-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR900003088B1 (ko) | 5-하이드록시피라졸 유도체 | |
| US5430169A (en) | Method for preparation of sphingoid bases | |
| RO107257B1 (ro) | Procedeu de obtinere a unui dihidrat de azitromicina, cristalin | |
| EP0483465B1 (de) | Langkettige Di(acyloxy)dialkylsilane, Di(acyloxy)diarylsilane, Di(acyloxy)dialkoxysilane und Tetra(acyloxy)silane, Verfahren zu ihrer Herstellung, ihre Verwendung zur Herstellung von Vesikeln, aus ihnen hergestellte Vesikel (Siosomen) und deren Verwendung als träger von Wirkstoffen | |
| CS244686B2 (en) | Preparation method of nonane or nonne | |
| CN107474021B (zh) | 噁二嗪衍生物及其制备方法和应用 | |
| DE10164564A1 (de) | Tetrahydrocarbazolderivate als Liganden für G-Protein gekoppelte Rezeptoren (GPCR) | |
| JPH07503479A (ja) | 除草剤としての，トリアゾール環を含有するホスホン酸誘導体 | |
| HU184622B (en) | Process for preparing 7/z/-dodecen-1-yl-acetate | |
| US3005823A (en) | 5-quinolyl methylcarbamate | |
| AT398568B (de) | Verfahren zur herstellung von methylendioxyphenanthren- und -stilbenderivaten | |
| US2765252A (en) | Synergistic bis-(dimethylamino)-fluorophosphine oxide insecticidal compositions | |
| DE2329092A1 (de) | N-substituierte prostaglandincarboxamide und verfahren zu deren herstellung | |
| CA1056384A (fr) | Derives thiazoliques organophosphores, procede de preparation | |
| JPS6230185B2 (xx) | ||
| IL41437A (en) | Phenyl and benzyl alkynyl ethers their production and pest-population control compositions containing them | |
| CN115466232A (zh) | (6z,9z)-3,4-环氧十九碳二烯的制备方法 | |
| EP1799642A1 (en) | Process and intermediates for the selective synthesis of fluvastatin | |
| US5023360A (en) | Simplified synthesis of dialkylgold(III) β-diketonates | |
| JP2933412B2 (ja) | ホスファチジルコリンの製造法 | |
| KR960010531B1 (ko) | 퍼메스린의 새로운 제조방법 | |
| GB2104061A (en) | 2,3-Dihydropyrans and methods for combatting insects therewith | |
| JP2689319B2 (ja) | キボシカミキリの性刺激剤 | |
| JPH0592982A (ja) | α−グリセロ−ホスホリル−コリンの光学活性ジアセチルエステル及びラセミ水和ジアセチルエステル | |
| Olszewski Claude Grison et al. | Synthesis of insect pheromones: Improved method for the preparation of queen substance and royal jelly of honeybees Apis mellifera |