FR2491920A1 - Nouveaux esters methyliques derives de l'acide 2,2-dimethyl cyclopropane 1,3-dicarboxylique, leur preparation et les intermediaires nouveaux obtenus - Google Patents
Nouveaux esters methyliques derives de l'acide 2,2-dimethyl cyclopropane 1,3-dicarboxylique, leur preparation et les intermediaires nouveaux obtenus Download PDFInfo
- Publication number
- FR2491920A1 FR2491920A1 FR8021690A FR8021690A FR2491920A1 FR 2491920 A1 FR2491920 A1 FR 2491920A1 FR 8021690 A FR8021690 A FR 8021690A FR 8021690 A FR8021690 A FR 8021690A FR 2491920 A1 FR2491920 A1 FR 2491920A1
- Authority
- FR
- France
- Prior art keywords
- cis
- acid
- dicarboxylic acid
- methyl
- mono
- 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.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 150000004702 methyl esters Chemical class 0.000 title claims abstract description 6
- MSPJNHHBNOLHOC-UHFFFAOYSA-N 3,3-dimethylcyclopropane-1,2-dicarboxylic acid Chemical compound CC1(C)C(C(O)=O)C1C(O)=O MSPJNHHBNOLHOC-UHFFFAOYSA-N 0.000 title claims description 9
- 239000000543 intermediate Substances 0.000 title abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 230000008569 process Effects 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 8
- 239000011707 mineral Substances 0.000 claims description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- MSPJNHHBNOLHOC-QWWZWVQMSA-N (1s,2s)-3,3-dimethylcyclopropane-1,2-dicarboxylic acid Chemical compound CC1(C)[C@@H](C(O)=O)[C@@H]1C(O)=O MSPJNHHBNOLHOC-QWWZWVQMSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 238000006317 isomerization reaction Methods 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 230000009471 action Effects 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 claims 1
- 230000000361 pesticidal effect Effects 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 150000002148 esters Chemical class 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- LNIQYJXNDLAPKL-UHFFFAOYSA-N 3-methoxycarbonyl-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound COC(=O)C1C(C(O)=O)C1(C)C LNIQYJXNDLAPKL-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- -1 monoethyl ester Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- ITNHSNMLIFFVQC-UHFFFAOYSA-N methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound COC(=O)C1C(C=C(C)C)C1(C)C ITNHSNMLIFFVQC-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- HYSOPXHRAHXSFM-UHFFFAOYSA-N (1-methylcyclohexa-2,4-dien-1-yl)methanamine Chemical compound NCC1(C)CC=CC=C1 HYSOPXHRAHXSFM-UHFFFAOYSA-N 0.000 description 1
- CJAAPVQEZPAQNI-UHFFFAOYSA-N (2-methylphenyl)methanamine Chemical compound CC1=CC=CC=C1CN CJAAPVQEZPAQNI-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 229930045534 Me ester-Cyclohexaneundecanoic acid Natural products 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- BFAKENXZKHGIGE-UHFFFAOYSA-N bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene Chemical compound FC1=C(C(=C(C(=C1F)I)F)F)N=NC1=C(C(=C(C(=C1F)F)I)F)F BFAKENXZKHGIGE-UHFFFAOYSA-N 0.000 description 1
- FDKLLWKMYAMLIF-UHFFFAOYSA-N cyclopropane-1,1-dicarboxylic acid Chemical class OC(=O)C1(C(O)=O)CC1 FDKLLWKMYAMLIF-UHFFFAOYSA-N 0.000 description 1
- RLWFMZKPPHHHCB-UHFFFAOYSA-N cyclopropane-1,2-dicarboxylate;hydron Chemical class OC(=O)C1CC1C(O)=O RLWFMZKPPHHHCB-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- ITNHSNMLIFFVQC-BDAKNGLRSA-N methyl (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical group COC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C ITNHSNMLIFFVQC-BDAKNGLRSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- HHBXWXJLQYJJBW-UHFFFAOYSA-M triphenyl(propan-2-yl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C(C)C)C1=CC=CC=C1 HHBXWXJLQYJJBW-UHFFFAOYSA-M 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8021690A FR2491920A1 (fr) | 1980-10-10 | 1980-10-10 | Nouveaux esters methyliques derives de l'acide 2,2-dimethyl cyclopropane 1,3-dicarboxylique, leur preparation et les intermediaires nouveaux obtenus |
| EP81401520A EP0050074B1 (fr) | 1980-10-10 | 1981-10-02 | Nouveaux esters méthyliques dérivés de l'acide 2,2-diméthyl cyclopropane 1,3-dicarboxylique, leur préparation et les intermédiaires nouveaux obtenus |
| US06/308,026 US4408066A (en) | 1980-10-10 | 1981-10-02 | Methyl cyclopropane-1,3-dicarboxylate |
| AT81401520T ATE8248T1 (de) | 1980-10-10 | 1981-10-02 | Methylester von 2,2-dimethyl-cyclopropan-1,3dicarbons[ure, verfahren zu ihrer herstellung und erhaltene zwischenprodukte. |
| DE8181401520T DE3164589D1 (en) | 1980-10-10 | 1981-10-02 | Methyl esters of 2,2-dimethyl cyclopropane-1,3-dicarboxylic acid, their preparation and intermediales obtained |
| CA000387678A CA1181414A (fr) | 1980-10-10 | 1981-10-09 | Esters methyliques derives de l'acide 2,2-dimethyl cyclopropane 1,3-dicarboxylique, et leur preparation |
| HU812925A HU194531B (en) | 1980-10-10 | 1981-10-09 | Process for producing esters of 2,2-dimethyl-cyclopropane-1,3-dicarboxylic acids |
| JP56161089A JPS57126445A (en) | 1980-10-10 | 1981-10-12 | Novel methyl ester derived from 2,2-dimethylcyclopropane-1,3-dicarboxylic acid, manufacture and obtained novel intermediate |
| US06/511,506 US4487955A (en) | 1980-10-10 | 1983-07-06 | Process for preparing cis or trans, optically active monoalkyl esters of cyclopropane-1,3-dicarboxylic acids |
| JP2182850A JPH0341053A (ja) | 1980-10-10 | 1990-07-12 | ２，２―ジメチルシクロプロパン―１，３―ジカルボン酸のモノメチルエステルのα―メチルベンジルアミン塩 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8021690A FR2491920A1 (fr) | 1980-10-10 | 1980-10-10 | Nouveaux esters methyliques derives de l'acide 2,2-dimethyl cyclopropane 1,3-dicarboxylique, leur preparation et les intermediaires nouveaux obtenus |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2491920A1 true FR2491920A1 (fr) | 1982-04-16 |
| FR2491920B1 FR2491920B1 (en, 2012) | 1983-11-04 |
Family
ID=9246750
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8021690A Granted FR2491920A1 (fr) | 1980-10-10 | 1980-10-10 | Nouveaux esters methyliques derives de l'acide 2,2-dimethyl cyclopropane 1,3-dicarboxylique, leur preparation et les intermediaires nouveaux obtenus |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4408066A (en, 2012) |
| EP (1) | EP0050074B1 (en, 2012) |
| JP (2) | JPS57126445A (en, 2012) |
| AT (1) | ATE8248T1 (en, 2012) |
| CA (1) | CA1181414A (en, 2012) |
| DE (1) | DE3164589D1 (en, 2012) |
| FR (1) | FR2491920A1 (en, 2012) |
| HU (1) | HU194531B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3541450A1 (de) * | 1985-11-23 | 1987-05-27 | Merck Patent Gmbh | Verfahren zur herstellung von enantiomeren |
| EP1535895B1 (en) * | 2002-07-17 | 2012-04-25 | Sumitomo Chemical Company, Limited | Process for production of formylcyclopropanecarboxylic esters |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE862461A (fr) * | 1976-12-30 | 1978-06-29 | Roussel Uclaf | Procede de preparation d'esters d'alcoyle inferieur d'acides cis ou trans 3-formyl cyclopropane 2,2-disubstitues racemiques |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2376119A1 (fr) * | 1976-12-30 | 1978-07-28 | Roussel Uclaf | Procede de preparation d'esters d'alcoyle inferieur d'acides trans cyclopropane-1,3-dicarboxyliques 2,2-disubstitues racemiques et nouveaux esters desdits acides |
-
1980
- 1980-10-10 FR FR8021690A patent/FR2491920A1/fr active Granted
-
1981
- 1981-10-02 US US06/308,026 patent/US4408066A/en not_active Expired - Lifetime
- 1981-10-02 AT AT81401520T patent/ATE8248T1/de not_active IP Right Cessation
- 1981-10-02 EP EP81401520A patent/EP0050074B1/fr not_active Expired
- 1981-10-02 DE DE8181401520T patent/DE3164589D1/de not_active Expired
- 1981-10-09 HU HU812925A patent/HU194531B/hu not_active IP Right Cessation
- 1981-10-09 CA CA000387678A patent/CA1181414A/fr not_active Expired
- 1981-10-12 JP JP56161089A patent/JPS57126445A/ja active Granted
-
1990
- 1990-07-12 JP JP2182850A patent/JPH0341053A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE862461A (fr) * | 1976-12-30 | 1978-06-29 | Roussel Uclaf | Procede de preparation d'esters d'alcoyle inferieur d'acides cis ou trans 3-formyl cyclopropane 2,2-disubstitues racemiques |
Non-Patent Citations (1)
| Title |
|---|
| EXBK/54 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0380788B2 (en, 2012) | 1991-12-26 |
| JPH039094B2 (en, 2012) | 1991-02-07 |
| ATE8248T1 (de) | 1984-07-15 |
| DE3164589D1 (en) | 1984-08-09 |
| HU194531B (en) | 1988-02-29 |
| JPH0341053A (ja) | 1991-02-21 |
| EP0050074A3 (en) | 1982-05-05 |
| EP0050074A2 (fr) | 1982-04-21 |
| US4408066A (en) | 1983-10-04 |
| EP0050074B1 (fr) | 1984-07-04 |
| FR2491920B1 (en, 2012) | 1983-11-04 |
| JPS57126445A (en) | 1982-08-06 |
| CA1181414A (fr) | 1985-01-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |