CA1123857A - 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
- CA1123857A CA1123857A CA331,952A CA331952A CA1123857A CA 1123857 A CA1123857 A CA 1123857A CA 331952 A CA331952 A CA 331952A CA 1123857 A CA1123857 A CA 1123857A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- carene
- compound
- preparation
- cyclopropane
- 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 14
- 238000002360 preparation method Methods 0.000 title claims description 8
- 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
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 claims abstract description 8
- 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
- 239000007858 starting material Substances 0.000 claims abstract description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 4
- 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 claims abstract description 3
- VTHIKKVKIVQWHV-UHFFFAOYSA-N chromium(6+) oxygen(2-) pyridine Chemical compound [O-2].[O-2].[O-2].[Cr+6].C1=CC=NC=C1 VTHIKKVKIVQWHV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- WBZSWEPBEZFTFI-UHFFFAOYSA-N 3-(2,2-dimethoxyethyl)-2,2-dimethylcyclopropane-1-carbaldehyde Chemical compound COC(OC)CC1C(C=O)C1(C)C WBZSWEPBEZFTFI-UHFFFAOYSA-N 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- -1 cyclopropane compound Chemical class 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 239000002728 pyrethroid Substances 0.000 abstract description 6
- 239000002917 insecticide Substances 0.000 abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000000707 stereoselective effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000244317 Tillandsia usneoides Species 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 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 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 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
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 231100001225 mammalian toxicity Toxicity 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/28—Saturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
- C07C47/37—Saturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
- C07C45/305—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation with halogenochromate reagents, e.g. pyridinium chlorochromate
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB30338/78 | 1978-07-19 | ||
| GB7830338 | 1978-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1123857A true CA1123857A (en) | 1982-05-18 |
Family
ID=10498515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA331,952A Expired CA1123857A (en) | 1978-07-19 | 1979-07-17 | Intermediate in the preparation of cyclopropanecarboxylate esters and process for its manufacture |
Country Status (13)
-
1979
- 1979-07-17 CH CH664879A patent/CH641138A5/de not_active IP Right Cessation
- 1979-07-17 ZA ZA00793612A patent/ZA793612B/xx unknown
- 1979-07-17 IT IT24429/79A patent/IT1122206B/it active
- 1979-07-17 NL NL7905555A patent/NL7905555A/nl not_active Application Discontinuation
- 1979-07-17 CA CA331,952A patent/CA1123857A/en not_active Expired
- 1979-07-17 IN IN517/DEL/79A patent/IN152615B/en unknown
- 1979-07-17 IL IL57822A patent/IL57822A/xx not_active IP Right Cessation
- 1979-07-17 FR FR7918457A patent/FR2431475A1/fr active Granted
- 1979-07-17 JP JP8995179A patent/JPS5515488A/ja active Granted
- 1979-07-17 AU AU48983/79A patent/AU527967B2/en not_active Ceased
- 1979-07-17 BE BE0/196340A patent/BE877747A/fr not_active IP Right Cessation
- 1979-07-17 DE DE19792928837 patent/DE2928837A1/de active Granted
- 1979-07-17 DK DK300779A patent/DK300779A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2928837C2 (enrdf_load_stackoverflow) | 1988-01-21 |
| IL57822A0 (en) | 1979-11-30 |
| AU4898379A (en) | 1980-01-24 |
| IL57822A (en) | 1982-04-30 |
| IN152615B (enrdf_load_stackoverflow) | 1984-02-25 |
| AU527967B2 (en) | 1983-03-31 |
| IT7924429A0 (it) | 1979-07-17 |
| JPS6223732B2 (enrdf_load_stackoverflow) | 1987-05-25 |
| JPS5515488A (en) | 1980-02-02 |
| ZA793612B (en) | 1980-07-30 |
| BE877747A (fr) | 1980-01-17 |
| IT1122206B (it) | 1986-04-23 |
| DE2928837A1 (de) | 1980-01-31 |
| FR2431475A1 (fr) | 1980-02-15 |
| FR2431475B1 (enrdf_load_stackoverflow) | 1984-02-10 |
| CH641138A5 (en) | 1984-02-15 |
| NL7905555A (nl) | 1980-01-22 |
| DK300779A (da) | 1980-01-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |