CA1123016A - Intermediate in the preparation of cyclopropanecarboxylate esters and process for its manufacture - Google Patents
Intermediate in the preparation of cyclopropanecarboxylate esters and process for its manufactureInfo
- Publication number
- CA1123016A CA1123016A CA331,953A CA331953A CA1123016A CA 1123016 A CA1123016 A CA 1123016A CA 331953 A CA331953 A CA 331953A CA 1123016 A CA1123016 A CA 1123016A
- Authority
- CA
- Canada
- Prior art keywords
- carene
- compound
- preparation
- formula
- manufacture
- 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
- 238000000034 method Methods 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- BQOFWKZOCNGFEC-BDAKNGLRSA-N (+)-Delta3-carene Chemical compound C1C(C)=CC[C@H]2C(C)(C)[C@@H]12 BQOFWKZOCNGFEC-BDAKNGLRSA-N 0.000 claims abstract description 6
- 229930006713 (+)-car-3-ene Natural products 0.000 claims abstract description 6
- BQOFWKZOCNGFEC-UHFFFAOYSA-N Delta3-Carene Natural products C1C(C)=CCC2C(C)(C)C12 BQOFWKZOCNGFEC-UHFFFAOYSA-N 0.000 claims abstract description 6
- BSDTVZZPJYPNDF-UHFFFAOYSA-N [1-(2,2-dimethoxyethyl)-2,2-dimethylcyclopropyl]methyl acetate Chemical compound COC(OC)CC1(COC(C)=O)CC1(C)C BSDTVZZPJYPNDF-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 3
- 235000013350 formula milk Nutrition 0.000 claims description 14
- -1 cyclopropane compound Chemical class 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 4
- 239000002728 pyrethroid Substances 0.000 abstract description 5
- 239000002917 insecticide Substances 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 6
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000005949 ozonolysis reaction Methods 0.000 description 2
- 230000000707 stereoselective effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- IVFIVADDYKRLKE-UHFFFAOYSA-N [3-(2,2-dimethoxyethyl)-2,2-dimethylcyclopropyl]methanol Chemical compound COC(OC)CC1C(CO)C1(C)C IVFIVADDYKRLKE-UHFFFAOYSA-N 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/315—Compounds having groups containing oxygen atoms singly bound to carbon atoms not being acetal carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7830371 | 1978-07-19 | ||
| GB30,371/78 | 1978-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1123016A true CA1123016A (en) | 1982-05-04 |
Family
ID=10498524
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA331,953A Expired CA1123016A (en) | 1978-07-19 | 1979-07-17 | Intermediate in the preparation of cyclopropanecarboxylate esters and process for its manufacture |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5515487A (en, 2012) |
| AU (1) | AU521243B2 (en, 2012) |
| BE (1) | BE877749A (en, 2012) |
| CA (1) | CA1123016A (en, 2012) |
| CH (1) | CH641136A5 (en, 2012) |
| DE (1) | DE2928838A1 (en, 2012) |
| DK (1) | DK300679A (en, 2012) |
| FR (1) | FR2431473A1 (en, 2012) |
| IL (1) | IL57821A (en, 2012) |
| IN (1) | IN152614B (en, 2012) |
| IT (1) | IT1122205B (en, 2012) |
| NL (1) | NL7905556A (en, 2012) |
| ZA (1) | ZA793611B (en, 2012) |
-
1979
- 1979-07-17 ZA ZA00793611A patent/ZA793611B/xx unknown
- 1979-07-17 IN IN516/DEL/79A patent/IN152614B/en unknown
- 1979-07-17 NL NL7905556A patent/NL7905556A/nl not_active Application Discontinuation
- 1979-07-17 FR FR7918459A patent/FR2431473A1/fr active Granted
- 1979-07-17 IL IL57821A patent/IL57821A/xx not_active IP Right Cessation
- 1979-07-17 CA CA331,953A patent/CA1123016A/en not_active Expired
- 1979-07-17 DK DK300679A patent/DK300679A/da not_active Application Discontinuation
- 1979-07-17 JP JP8995079A patent/JPS5515487A/ja active Granted
- 1979-07-17 IT IT24428/79A patent/IT1122205B/it active
- 1979-07-17 CH CH665079A patent/CH641136A5/de not_active IP Right Cessation
- 1979-07-17 BE BE0/196342A patent/BE877749A/fr not_active IP Right Cessation
- 1979-07-17 AU AU48984/79A patent/AU521243B2/en not_active Ceased
- 1979-07-17 DE DE19792928838 patent/DE2928838A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IL57821A (en) | 1982-01-31 |
| ZA793611B (en) | 1980-07-30 |
| IT1122205B (it) | 1986-04-23 |
| AU4898479A (en) | 1980-01-24 |
| NL7905556A (nl) | 1980-01-22 |
| DE2928838A1 (de) | 1980-01-31 |
| IL57821A0 (en) | 1979-11-30 |
| JPS5515487A (en) | 1980-02-02 |
| IN152614B (en, 2012) | 1984-02-25 |
| DE2928838C2 (en, 2012) | 1988-01-21 |
| JPS6217575B2 (en, 2012) | 1987-04-18 |
| CH641136A5 (en) | 1984-02-15 |
| FR2431473B1 (en, 2012) | 1981-11-13 |
| FR2431473A1 (fr) | 1980-02-15 |
| AU521243B2 (en) | 1982-03-25 |
| BE877749A (fr) | 1980-01-17 |
| IT7924428A0 (it) | 1979-07-17 |
| DK300679A (da) | 1980-01-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |