Reacción #1946549

Ecuación de reacción

sodium hydroxide

ethyl (2E,4Z)-2,4-decadienoate

→

(2E,4Z)-2,4-decadienoic acid

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was heated
2. 2
   Temperaturaunder reflux for 5 hours
3. 3
   Otrotetrahydrofuran was removed on a rotary evaporator
4. 4
   workup.ADDITIONthe residue was diluted with water (100 ml)
5. 5
   ExtracciónThe acid was extracted with ether (3×100 ml)
6. 6
   Lavadothe combined extracts were washed with water (2×50 ml) and brine (50 ml)
7. 7
   Otrodried
8. 8
   OtroRemoval of ether under reduced pressure

Procedimiento

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.

Fuente