Sodium Hydroxide → Stillingic acid
Reaktionsgleichung
[OH-].[Na+].[C:3]([O:14]CC)(=[O:13])/[CH:4]=[CH:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>O1CCCC1>[C:3]([OH:14])(=[O:13])/[CH:4]=[CH:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
An aqueous solution of sodium hydroxide (10%, 22 ml) was added to a solution of technical grade ethyl (2E,4Z)-2,4-decadienoate (10 g) in tetrahydrofuran (100 ml). The mixture was heated under reflux for 5 hours with rapid stirring in a nitrogen atmosphere. After allowing to cool to room temperature, tetrahydrofuran was removed on a rotary evaporator, the residue was diluted with water (100 ml), and acidified to pH 2 with 6N HCl. The acid was extracted with ether (3×100 ml) and the combined extracts were washed with water (2×50 ml) and brine (50 ml) and dried using anhydrous magnesium sulfate. Removal of ether under reduced pressure gave (2E,4Z)-2,4-decadienoic acid. This product was used in the next step without further purification.