Reacción #2028904

ord-dcdde2e59fe347179fad14f9964efd49

Ecuación de reacción

CCOc1ccc(-c2ccc(C=COC)c(F)c2F)c(F)c1F
4-Ethoxy-2,2′,3,3′-tetrafluoro-4′-(2-methoxyvinyl)biphenyl
CCOc1ccc(-c2ccc(C=COC)c(F)c2F)c(F)c1F
4-ethoxy-2,2′,3,3′-tetrafluoro-4′-(2-methoxyvinyl)biphenyl
Cl
hydrochloric acid
O
Water
CCOc1ccc(-c2ccc(CC=O)c(F)c2F)c(F)c1F
2-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)acetoaldehyde
Rendimiento 97.2%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Extracciónthe water layer was extracted with toluene (100 ml) three times
  2. 2
    LavadoThe combined organic layer was washed with water
  3. 3
    Secadodried over anhydrous magnesium sulfate
  4. 4
    workup.DISTILLATIONThe solvent was distilled off under reduced pressure

Procedimiento

4-Ethoxy-2,2′,3,3′-tetrafluoro-4′-(2-methoxyvinyl)biphenyl (8) (18.5 g) prepared in the sixth step was dissolved in acetone (200 ml) and hydrochloric acid (6M; 200 ml) was added, and the stirring was continued at room temperature for 1 hour. Water (200 ml) was added, and the water layer was extracted with toluene (100 ml) three times. The combined organic layer was washed with water and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to leave 2-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)acetoaldehyde (9) (17.2 g) in 97.2% yield.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08389073B2uspto-grants-2013_03