CH618415A5 - Process for the preparation of novel 2,2-dimethyl-3,5,5,5-tetrachloropentane-1-carboxylic esters - Google Patents
Process for the preparation of novel 2,2-dimethyl-3,5,5,5-tetrachloropentane-1-carboxylic esters Download PDFInfo
- Publication number
- CH618415A5 CH618415A5 CH1374475A CH1374475A CH618415A5 CH 618415 A5 CH618415 A5 CH 618415A5 CH 1374475 A CH1374475 A CH 1374475A CH 1374475 A CH1374475 A CH 1374475A CH 618415 A5 CH618415 A5 CH 618415A5
- Authority
- CH
- Switzerland
- Prior art keywords
- dimethyl
- carboxylic acid
- complex
- benzoin
- dichloroethenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- DKFGXLPITKDNNE-UHFFFAOYSA-N 4,6,6,6-tetrachloro-3,3-dimethylhexanoic acid Chemical class OC(=O)CC(C)(C)C(Cl)CC(Cl)(Cl)Cl DKFGXLPITKDNNE-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 alkyl radical Chemical class 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 229960002130 benzoin Drugs 0.000 claims description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- FYYOTZLMLLTWAP-UHFFFAOYSA-N 3,3-dimethylpent-4-enoic acid Chemical compound C=CC(C)(C)CC(O)=O FYYOTZLMLLTWAP-UHFFFAOYSA-N 0.000 claims description 3
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 claims description 3
- LLMLSUSAKZVFOA-UJURSFKZSA-N (1S,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@@H]1C(O)=O LLMLSUSAKZVFOA-UJURSFKZSA-N 0.000 claims description 2
- 125000005265 dialkylamine group Chemical group 0.000 claims description 2
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 claims description 2
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical group Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- GEHLEADVHVVTET-UHFFFAOYSA-N ethyl(methyl)azanium;chloride Chemical compound [Cl-].CC[NH2+]C GEHLEADVHVVTET-UHFFFAOYSA-N 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- KTOQRRDVVIDEAA-UHFFFAOYSA-N 2-methylpropane Chemical compound [CH2]C(C)C KTOQRRDVVIDEAA-UHFFFAOYSA-N 0.000 claims 1
- PTQGFDXPHNRDCV-UHFFFAOYSA-N 3-formyl-2,2-dimethylcyclopropane-1-carboxylic acid Chemical class CC1(C)C(C=O)C1C(O)=O PTQGFDXPHNRDCV-UHFFFAOYSA-N 0.000 claims 1
- XNHFCOJLOKLPDO-UHFFFAOYSA-N C1(=CC=CC=C1)C(=O)C(O)C1=CC=CC=C1.Cl Chemical compound C1(=CC=CC=C1)C(=O)C(O)C1=CC=CC=C1.Cl XNHFCOJLOKLPDO-UHFFFAOYSA-N 0.000 claims 1
- XLOPRKKSAJMMEW-SFYZADRCSA-N Chrysanthemic acid Natural products CC(C)=C[C@@H]1[C@@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-N 0.000 claims 1
- 235000007516 Chrysanthemum Nutrition 0.000 claims 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 claims 1
- 238000007239 Wittig reaction Methods 0.000 claims 1
- VXSIXFKKSNGRRO-MXOVTSAMSA-N [(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1.CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VXSIXFKKSNGRRO-MXOVTSAMSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- QKYLHOOIOJOCIQ-UHFFFAOYSA-N cyclopropyl hydrogen carbonate Chemical compound OC(=O)OC1CC1 QKYLHOOIOJOCIQ-UHFFFAOYSA-N 0.000 claims 1
- PFBUKDPBVNJDEW-UHFFFAOYSA-N dichlorocarbene Chemical group Cl[C]Cl PFBUKDPBVNJDEW-UHFFFAOYSA-N 0.000 claims 1
- VVBOKSZMMZPBIY-UHFFFAOYSA-N dichloromethylidene(triphenyl)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=C(Cl)Cl)C1=CC=CC=C1 VVBOKSZMMZPBIY-UHFFFAOYSA-N 0.000 claims 1
- 230000000749 insecticidal effect Effects 0.000 claims 1
- 239000002917 insecticide Substances 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 238000005949 ozonolysis reaction Methods 0.000 claims 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 claims 1
- 229940070846 pyrethrins Drugs 0.000 claims 1
- 239000002728 pyrethroid Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 8
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 244000028419 Styrax benzoin Species 0.000 description 3
- 235000000126 Styrax benzoin Nutrition 0.000 description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000019382 gum benzoic Nutrition 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- GTTSNKDQDACYLV-UHFFFAOYSA-N Trihydroxybutane Chemical compound CCCC(O)(O)O GTTSNKDQDACYLV-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- ZLDOMUPTDYCDBS-UHFFFAOYSA-N ethyl 3,3-dimethylpent-4-enoate Chemical compound CCOC(=O)CC(C)(C)C=C ZLDOMUPTDYCDBS-UHFFFAOYSA-N 0.000 description 1
- IKYLWHDWLWHILP-UHFFFAOYSA-N ethyl 4,6,6,6-tetrachloro-3,3-dimethylhexanoate Chemical compound CCOC(=O)CC(C)(C)C(Cl)CC(Cl)(Cl)Cl IKYLWHDWLWHILP-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/63—Halogen-containing esters of saturated acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12224274A JPS5159839A (ja) | 1974-10-23 | 1974-10-23 | Shikuropuropankarubonsanjudotaino seizoho |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH618415A5 true CH618415A5 (en) | 1980-07-31 |
Family
ID=14831096
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1374475A CH618415A5 (en) | 1974-10-23 | 1975-10-23 | Process for the preparation of novel 2,2-dimethyl-3,5,5,5-tetrachloropentane-1-carboxylic esters |
| CH946379A CH624920A5 (en) | 1974-10-23 | 1979-10-22 | Process for the preparation of trans-2,2-dimethyl-3-(2,2-dichloroethenyl)cyclopropane-1-carboxylic acid and its esters |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH946379A CH624920A5 (en) | 1974-10-23 | 1979-10-22 | Process for the preparation of trans-2,2-dimethyl-3-(2,2-dichloroethenyl)cyclopropane-1-carboxylic acid and its esters |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5159839A (enrdf_load_stackoverflow) |
| CH (2) | CH618415A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2547510A1 (enrdf_load_stackoverflow) |
| FR (2) | FR2313347A1 (enrdf_load_stackoverflow) |
| GB (2) | GB1512419A (enrdf_load_stackoverflow) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5822463B2 (ja) * | 1975-03-11 | 1983-05-09 | ザイダンホウジン サガミチユウオウカガクケンキユウシヨ | チカンビニルキオユウスル シクロプロパンカルボンサンユウドウタイノセイホウ |
| US4681953A (en) * | 1974-09-10 | 1987-07-21 | Sagami Chemical Research Center | Process for preparing dihalovinylcyclopropanecarboxylates |
| NZ180822A (en) * | 1975-05-16 | 1979-03-16 | Ici Ltd | Preparation of 2-(2,2-dihalovinyl)-3,3-dimethylcyolopropane carboxylates intermediates |
| GB1580204A (en) * | 1976-07-07 | 1980-11-26 | Shell Int Research | 2-cyanohexanoic acid derivatives |
| NZ185635A (en) * | 1976-11-18 | 1980-04-28 | Ici Ltd | Preparation of 3-dihalovinyl-2,2-dimethylcyclopropane carboxylic acid derivatives |
| FR2380244A1 (fr) * | 1977-02-11 | 1978-09-08 | Ciba Geigy Ag | Composes cyclopropane-carbonyliques utiles a la preparation de composes appropries a la lutte contre les parasites |
| US4390547A (en) | 1978-07-11 | 1983-06-28 | Kuraray Co., Ltd. | 2,2-Dimethyl-3-(substituted ethyl)cyclopropane carboxylate pesticidal compositions and methods |
| JPS5459261A (en) * | 1978-10-02 | 1979-05-12 | Kuraray Co Ltd | Substituted cyclopropanecarboxylic acid derivative |
| EP0010875B1 (en) * | 1978-10-27 | 1983-06-22 | Imperial Chemical Industries Plc | Process of separating cis and trans isomers of cyclopropane carboxylic acids |
| EP0010859B1 (en) * | 1978-10-31 | 1982-12-01 | Imperial Chemical Industries Plc | Process for the preparation of cyclopropane carboxylic acid esters |
| DE2923776A1 (de) * | 1979-06-12 | 1980-12-18 | Bayer Ag | Verfahren zur herstellung von 3,3-dimethyl-cyclopropan-1,2-dicarbonsaeureestern sowie zwischenprodukte zu deren herstellung |
| DE2923777A1 (de) * | 1979-06-12 | 1980-12-18 | Bayer Ag | Verfahren zur herstellung von 2-cyano-3,3-dimethyl-cyclopropan-1- carbonsaeureestern sowie zwischenprodukte zu seiner durchfuehrung |
| CN106316824B (zh) * | 2016-08-18 | 2018-10-19 | 广州康瑞泰药业有限公司 | 一种合成2-氟环丙烷甲酸的新方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1269127A (fr) * | 1960-06-20 | 1961-08-11 | Rhone Poulenc Sa | Procédé de préparation de l'acide chrysanthémique |
| FR1356949A (fr) * | 1962-12-13 | 1964-04-03 | Rhone Poulenc Sa | Procédé de préparation de dérivés de l'acide cyclopropanecarboxylique |
| JPS5822463B2 (ja) * | 1975-03-11 | 1983-05-09 | ザイダンホウジン サガミチユウオウカガクケンキユウシヨ | チカンビニルキオユウスル シクロプロパンカルボンサンユウドウタイノセイホウ |
| JPS5545062B2 (enrdf_load_stackoverflow) * | 1974-09-10 | 1980-11-15 |
-
1974
- 1974-10-23 JP JP12224274A patent/JPS5159839A/ja active Granted
-
1975
- 1975-10-23 FR FR7532410A patent/FR2313347A1/fr active Granted
- 1975-10-23 GB GB4366475A patent/GB1512419A/en not_active Expired
- 1975-10-23 GB GB2821676A patent/GB1512420A/en not_active Expired
- 1975-10-23 DE DE19752547510 patent/DE2547510A1/de not_active Ceased
- 1975-10-23 CH CH1374475A patent/CH618415A5/de not_active IP Right Cessation
-
1976
- 1976-07-23 FR FR7622534A patent/FR2309508A1/fr active Granted
-
1979
- 1979-10-22 CH CH946379A patent/CH624920A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2313347B1 (enrdf_load_stackoverflow) | 1979-07-13 |
| JPS5234619B2 (enrdf_load_stackoverflow) | 1977-09-05 |
| FR2309508B1 (enrdf_load_stackoverflow) | 1979-07-27 |
| FR2309508A1 (fr) | 1976-11-26 |
| DE2547510A1 (de) | 1976-04-29 |
| CH624920A5 (en) | 1981-08-31 |
| GB1512419A (en) | 1978-06-01 |
| GB1512420A (en) | 1978-06-01 |
| FR2313347A1 (fr) | 1976-12-31 |
| JPS5159839A (ja) | 1976-05-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUE | Assignment |
Owner name: SAGAMI CHEMICAL RESEARCH CENTER |
|
| PL | Patent ceased | ||
| PL | Patent ceased |