Reacción #1824340

Ecuación de reacción

xylene

triphenyl phosphine

8-bromooctanoic acid

→

11,11-dimethyldodecan-8-enoic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroremoving the solvent
2. 2
   workup.DISSOLUTIONThe residue was dissolved in THF (20 ml)/DMSO (2 ml) and butyllithium (2.5M; 4 ml) in hexane (4 ml)
3. 3
   workup.ADDITIONwas added dropwise at 0° C
4. 4
   workup.ADDITIONwas added dropwise
5. 5
   workup.ADDITIONWater and dilute hydrochloric acid were added
6. 6
   Extracciónthe mixture extracted with diethyl ether(x3)

Procedimiento

8-triphenylphosphonium octanoic acid bromide salt (2.43 g) was prepared by reacting triphenyl phosphine with 8-bromooctanoic acid in xylene solvent under reflux conditions, and removing the solvent. The residue was dissolved in THF (20 ml)/DMSO (2 ml) and butyllithium (2.5M; 4 ml) in hexane (4 ml) was added dropwise at 0° C. After warming to room temperature over 30 minutes 3,3-dimethylbutanal (0.5 g) in THF (5 ml) was added dropwise and the mixture stirred at room temperature for 3 hours. Water and dilute hydrochloric acid were added and the mixture extracted with diethyl ether(x3). Pure product 11,11-dimethyldodecan-8-enoic acid (0.4 g) was provided after silica gel column chromatography.

Fuente