Réaction #2028905

Équation de réaction

2-(4′-Ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)acetoaldehyde

2-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)acetoaldehyde

Jones reagent

isopropyl alcohol

→

2-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)acetic acid

Rendement 75.2%

Solvants

acetone

Conditions de réaction

Traitement

1. 1
   Températurethe solution was cooled on an ice bath
2. 2
   workup.WAITthe stirring was continued for 30 minutes
3. 3
   FiltrationThe reaction mixture was filtered through Celite, and water (200 ml) and ethyl acetate (100 ml)
4. 4
   workup.ADDITIONwere added to filtrate
5. 5
   Autreto give two layers
6. 6
   ExtractionThe water layer was extracted with ethyl acetate (50 ml) three times
7. 7
   Lavagethe combined organic layer was washed with water
8. 8
   SéchageThe solution was dried over anhydrous magnesium sulfate
9. 9
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
10. 10
    AutreThe residue was purified by means of back-extraction

Mode opératoire

2-(4′-Ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)acetoaldehyde (9) (17.2 g) prepared in the seventh step was dissolved in acetone (150 ml) and the solution was cooled on an ice bath. The Jones reagent (2.67M; 35 ml) was added to the solution. After 2 hours of stirring, isopropyl alcohol (10 ml) was added, and the stirring was continued for 30 minutes. The reaction mixture was filtered through Celite, and water (200 ml) and ethyl acetate (100 ml) were added to filtrate to give two layers. The water layer was extracted with ethyl acetate (50 ml) three times, and the combined organic layer was washed with water. The solution was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by means of back-extraction to give 2-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)acetic acid (10) (13.6 g) in 75.2% yield.

Source