Epimerization of trans chrysanthemates
US4447637A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Feb 9, 1982 |
| Grant date | May 8, 1984 |
| Priority date | — |
| Expiry date | Feb 9, 2002 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C51/487
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A novel process for the epimerization of alkyl trans chrysanthemates comprising reacting at a low temperature in an anhydrous organic solvent an alkyl trans chrysanthemate of the formula ##STR1## of the 1S, trans or 1R, trans configuration wherein R is alkyl of 1 to 6 carbon atoms with a strong alkali metal base to obtain a compound of the formula ##STR2## wherein R has the above definition and M is an alkali metal, reacting the latter compound with a reactant of the formula EQU Y--A wherein A is selected from the group consisting of chlorine, bromine, iodine and anion derived from a hydrogen acid and Y is an organic radical capable of forming a ketal of a ketene to obtain a compound of the formula ##STR3## reacting the latter at a low temperature in an anhydrous organic solvent with a proton donor to obtain a mixture of the corresponding alkyl cis chrysanthemate and alkyl trans chrysanthemate and recovering the cis chrysanthemic acid of the formula ##STR4## with the 1R, cis or 1S, cis configuration.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.