UST102907I4 - Process to 3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate - Google Patents
Process to 3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate Download PDFInfo
- Publication number
- UST102907I4 UST102907I4 US06/381,997 US38199782A UST102907I4 US T102907 I4 UST102907 I4 US T102907I4 US 38199782 A US38199782 A US 38199782A US T102907 I4 UST102907 I4 US T102907I4
- Authority
- US
- United States
- Prior art keywords
- lower alkyl
- dichlorovinyl
- product
- dimethylcyclopropanecarboxylate
- phenoxybenzyl
- 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.)
- Pending
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
3-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate is prepared in greater than 90% yield by alcoholysis of lower alkyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylates with 3-phenoxybenzyl alcohol. A lower alkyl alcohol, e.g., methanol or ethanol, is generated as a by-product.
The process is conducted under reflux at a temperature of at least 100° C. in an inert solvent between approximately stoichiometric amounts of the reactants. The solvent is selected to form an azeotropic mixture with, or boil at a higher temperature than, the lower alkyl alcohol by-product, and the by-product is removed from the mixture by distillation as it is produced. If lower alkyl is methyl or ethyl, n-octane, benzene, toluene, xylene, or mesitylene may be employed, for example.
The process is promoted by lower alkyl titanium alkoxide catalysts. The purity of the product 3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate, which is obtained as a bottoms residue after stripping the solvent, is high enough, greater than 90%, to be suitable for use in commerce as the pyrethroid insecticide "permethrin" without further purification. The purity is enhanced by the use of only 0.001-0.01 mole of the catalyst per mole of lower alkyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate. To avoid hydrolysis of the catalyst, the reaction is carried out under substantially anhydrous conditions.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/381,997 UST102907I4 (en) | 1979-02-07 | 1982-05-25 | Process to 3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1018379A | 1979-02-07 | 1979-02-07 | |
| US06/381,997 UST102907I4 (en) | 1979-02-07 | 1982-05-25 | Process to 3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US1018379A Continuation | 1979-02-07 | 1979-02-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UST102907I4 true UST102907I4 (en) | 1983-04-05 |
Family
ID=26680880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/381,997 Pending UST102907I4 (en) | 1979-02-07 | 1982-05-25 | Process to 3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | UST102907I4 (en) |
-
1982
- 1982-05-25 US US06/381,997 patent/UST102907I4/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4133833A (en) | Production of N,N-di(ethyl)-meta-toluamide from meta-toluic acid by liquid phase catalytic reaction with diethylamine | |
| KR101210196B1 (en) | Method for the production of formic acid | |
| CA1241662A (en) | Process for the preparation of sterically hindered hydroxyphenylcarboxylic acid esters | |
| Nozakura et al. | Cyanoethylation of Trichlorosilane. I. β-Addition. | |
| US4618700A (en) | Process for the preparation of a hydroxyphenylcarboxylate | |
| GB2039286A (en) | Preparation of monomeric organosilicon esters | |
| UST102907I4 (en) | Process to 3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate | |
| JPS5826331B2 (en) | Method for producing stereo-regulated farnesyl acetate | |
| US4301297A (en) | Process for preparing dimethylaminoethyl methacrylate | |
| US4520209A (en) | Process for cyclizing upsilon-chlorocarboxylic acids | |
| US3943167A (en) | Process for preparing trans-chrysanthemic acid | |
| US4116998A (en) | Preparation of esters of m-phenoxybenzyl alcohol and its α-cyano and α-ethinyl derivatives with 2,2-dimethylcyclopropanecarboxylic acids | |
| JPH03109354A (en) | Preparation of alkoxyalkylidenemalonic acid dialkyl ester | |
| CA1123855A (en) | Process to 3-phenoxybenzyl 3-(2,2-dihalovinyl)-2,2-dimethylcyclopropane- carboxylate | |
| GB1571388A (en) | Manufacture of esters | |
| US4906769A (en) | Isomerization of 2-pentenoates to 3-pentenoates | |
| JPH0261445B2 (en) | ||
| US3118953A (en) | 1, 3-di-(p-cyclopenten-2-yl-phenoxy)-propanol-2 | |
| US4250326A (en) | Method of reducing the contents of haloethynyl-containing impurities in synthetic dihaloethenyl pyrethroid insecticides or intermediates by reaction with phosphites | |
| EP0003624B1 (en) | Process for the preparation of the methyl ester of 4-oxopentane-1-carboxylic acid | |
| US6002062A (en) | Process for the preparation of ethynylcyclopropane | |
| IE58213B1 (en) | Process for preparing 4-substituted phthalic anhydrides | |
| EP0163533B1 (en) | Process for preparing adducts of alcohols, ethers and esters with 1,2-dichlorodifluoroethylene | |
| CA2092347A1 (en) | Process for the production of tetronic acid alkyl esters | |
| US3259648A (en) | Cyclohexylmethyl cinnamate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| STCF | Information on status: patent grant |
Free format text: PATENTED CASE |