CH645338A5 - Esteri dell'acido 2,2-dimetil-3-acetossimetil-ciclopropancarbossilico e loro preparazione. - Google Patents
Esteri dell'acido 2,2-dimetil-3-acetossimetil-ciclopropancarbossilico e loro preparazione. Download PDFInfo
- Publication number
- CH645338A5 CH645338A5 CH527980A CH527980A CH645338A5 CH 645338 A5 CH645338 A5 CH 645338A5 CH 527980 A CH527980 A CH 527980A CH 527980 A CH527980 A CH 527980A CH 645338 A5 CH645338 A5 CH 645338A5
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- diazoacetate
- dimethyl
- process according
- cyclohexane
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 6
- QAQLHYRDSMNRDZ-UHFFFAOYSA-N 3-acetyloxy-1,2,2-trimethylcyclopropane-1-carboxylic acid Chemical compound C(C)(=O)OC1C(C1(C(=O)O)C)(C)C QAQLHYRDSMNRDZ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 11
- XXIKYCPRDXIMQM-UHFFFAOYSA-N Isopentenyl acetate Chemical compound CC(C)=CCOC(C)=O XXIKYCPRDXIMQM-UHFFFAOYSA-N 0.000 claims description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 9
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- BXEFQPCKQSTMKA-UHFFFAOYSA-N OC(=O)C=[N+]=[N-] Chemical compound OC(=O)C=[N+]=[N-] BXEFQPCKQSTMKA-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 239000010949 copper Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- DRBHABDFIYSLEV-UHFFFAOYSA-N 3-(acetyloxymethyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC(=O)OCC1C(C(O)=O)C1(C)C DRBHABDFIYSLEV-UHFFFAOYSA-N 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- YVPJCJLMRRTDMQ-UHFFFAOYSA-N ethyl diazoacetate Chemical compound CCOC(=O)C=[N+]=[N-] YVPJCJLMRRTDMQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 239000012299 nitrogen atmosphere Substances 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GZVJRUASQZSDKH-UHFFFAOYSA-N 3-(hydroxymethyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(CO)C1C(O)=O GZVJRUASQZSDKH-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 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
- SHCSFZHSNSGTOP-UHFFFAOYSA-N Methyl 4-pentenoate Chemical compound COC(=O)CCC=C SHCSFZHSNSGTOP-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- MCCGVJDWZCZTJV-UHFFFAOYSA-N propan-2-ylphosphanium Chemical compound C[C-](C)[PH3+] MCCGVJDWZCZTJV-UHFFFAOYSA-N 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT24225/79A IT1122093B (it) | 1979-07-10 | 1979-07-10 | Esteri dell'acido 2,2-dimetil-3-acetossimetil-ciclopropancarbossilico e loro preparazione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH645338A5 true CH645338A5 (it) | 1984-09-28 |
Family
ID=11212646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH527980A CH645338A5 (it) | 1979-07-10 | 1980-07-10 | Esteri dell'acido 2,2-dimetil-3-acetossimetil-ciclopropancarbossilico e loro preparazione. |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5625137A (fr) |
| BE (1) | BE884260A (fr) |
| CH (1) | CH645338A5 (fr) |
| DE (1) | DE3026011A1 (fr) |
| FR (1) | FR2460918A1 (fr) |
| GB (1) | GB2054587B (fr) |
| IT (1) | IT1122093B (fr) |
| NL (1) | NL8003910A (fr) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5119747A (en) * | 1974-08-09 | 1976-02-17 | Sumitomo Chemical Co | 2*22 jimechiru 33 * 2**2** jikurorubiniru * shikuropuropankarubonsanesuteruno seizohoho |
-
1979
- 1979-07-10 IT IT24225/79A patent/IT1122093B/it active
-
1980
- 1980-07-07 NL NL8003910A patent/NL8003910A/nl not_active Application Discontinuation
- 1980-07-08 FR FR8015128A patent/FR2460918A1/fr active Granted
- 1980-07-08 JP JP9232280A patent/JPS5625137A/ja active Pending
- 1980-07-09 DE DE19803026011 patent/DE3026011A1/de not_active Withdrawn
- 1980-07-09 GB GB8022436A patent/GB2054587B/en not_active Expired
- 1980-07-10 BE BE0/201361A patent/BE884260A/fr not_active IP Right Cessation
- 1980-07-10 CH CH527980A patent/CH645338A5/it not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL8003910A (nl) | 1981-01-13 |
| FR2460918A1 (fr) | 1981-01-30 |
| JPS5625137A (en) | 1981-03-10 |
| GB2054587B (en) | 1983-07-13 |
| FR2460918B1 (fr) | 1984-03-30 |
| BE884260A (fr) | 1981-01-12 |
| IT1122093B (it) | 1986-04-23 |
| IT7924225A0 (it) | 1979-07-10 |
| GB2054587A (en) | 1981-02-18 |
| DE3026011A1 (de) | 1981-02-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |