Method of preparing 2,6,10-Trimethyl-1,1-dialkoxy-3,5,9-undecatriene used as an intermediate of lycopene
US9051254B2 · kind B2 · utility
Assignees
Inventors
Key dates
| Filing date | Jun 11, 2012 |
| Grant date | Jun 9, 2015 |
| Priority date | — |
| Expiry date | Jul 16, 2033 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C41/48
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
The present invention describes a novel synthetic method for preparing the key intermediate 2,6,10-trimethyl-1,1-dialkoxy-3,5,9-undecatriene of lycopene. An existing synthetic method have some disadvantages that it is very difficult to gain the raw material dialkyl 4-methyl-5,5-diakoxy-1-pentene-1-phosphonate (10) because no effective synthetic method can be adopted, and furthermore the obtained target compound is composed of several cis/trans isomers. This invention relates to a process comprising a condensation step wherein a starting C10-phosphonate is changed to its carbanion completely at a temperature of −40˜30 under an atmosphere of a non-reactive gas in an organic solvent catalyzed by base, and then C4-dialkyl is added to undergo Wittig-Horner condensation. This invention affords all trans C14-acetal and this method is characterized with the advantages of simple procedure, easy access to raw material and low cost, which makes it has the value of industrial application.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.