UST102908I4 - Catalyzed transesterification synthesis - Google Patents
Catalyzed transesterification synthesis Download PDFInfo
- Publication number
- UST102908I4 UST102908I4 US06/382,007 US38200782A UST102908I4 US T102908 I4 UST102908 I4 US T102908I4 US 38200782 A US38200782 A US 38200782A US T102908 I4 UST102908 I4 US T102908I4
- Authority
- US
- United States
- Prior art keywords
- lower alkyl
- formula
- catalyst
- carbon atoms
- phenoxy
- 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
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Esters of the formula ##STR1## wherein X is chlorine or bromine and B is a benzyl group of the formula ##STR2## where Y and Z may be the same or different and are selected from the group consisting of hydrogen, halogen, lower alkyl, lowr alkoxy, phenyl, phenoxy, lower alkyl phenyl, lower alkyl phenoxy, halophenyl and halophenoxy, are prepared by transesterification between BOH and a compound of the formula ##STR3## wherein L is a lower alkyl radical of between 1 and 4 carbon atoms, using as catalyst an organometallic compound selected from (RO)4 Ti and R'2 SnO, where R and R' are alkyl radicals of between 1 and 6 carbon atoms.
Useful organometallic catalysts include tetrabutyl titanate, tetraisopropyl titanate, and dibutyl tin(IV)oxide. About 1% by weight of the total charge of reactants is catalyst.
The process is conducted at 100°-200° C. under vacuum, generally in the absence of solvent, with sustained distillation of the LOH by-product until the theoretical amount of alcohol is collected. The product ester is then distilled under vacuum.
For example, 126 g ethyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate, 100 g m-phenoxybenzyl alcohol, and 2.25 grams of tetraisopropyl titanate reacted at 150° C./200 mm Hg yielded the m-phenoxybenzyl ester; bp 181° C./0.1 mm Hg, 89% yield, 99.5% pure.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/382,007 UST102908I4 (en) | 1977-05-27 | 1982-05-25 | Catalyzed transesterification synthesis |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80134577A | 1977-05-27 | 1977-05-27 | |
| US06/382,007 UST102908I4 (en) | 1977-05-27 | 1982-05-25 | Catalyzed transesterification synthesis |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US80134577A Continuation | 1977-05-27 | 1977-05-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UST102908I4 true UST102908I4 (en) | 1983-04-05 |
Family
ID=27009596
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/382,007 Pending UST102908I4 (en) | 1977-05-27 | 1982-05-25 | Catalyzed transesterification synthesis |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | UST102908I4 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5147645A (en) * | 1988-06-21 | 1992-09-15 | Basf Aktiengesellschaft | Pyrethroids and their use for controlling pests |
| US6441220B1 (en) * | 1999-06-16 | 2002-08-27 | Sumitomo Chemical Company, Limited | Methods for producing cyclopropane carboxylates |
-
1982
- 1982-05-25 US US06/382,007 patent/UST102908I4/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5147645A (en) * | 1988-06-21 | 1992-09-15 | Basf Aktiengesellschaft | Pyrethroids and their use for controlling pests |
| US6441220B1 (en) * | 1999-06-16 | 2002-08-27 | Sumitomo Chemical Company, Limited | Methods for producing cyclopropane carboxylates |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| STCF | Information on status: patent grant |
Free format text: PATENTED CASE |