Reaction #2028904

Reaction equation

4-Ethoxy-2,2′,3,3′-tetrafluoro-4′-(2-methoxyvinyl)biphenyl

4-ethoxy-2,2′,3,3′-tetrafluoro-4′-(2-methoxyvinyl)biphenyl

hydrochloric acid

Water

→

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

Yield 97.2%

Solvents

acetone

Conditions

Workup

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

Procedure

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.

Source