Hydrochloric Acid → 2-(4'-Ethoxy-2,2',3,3'-tetrafluorobiphenyl-4-yl)acetoaldehyde

HRID 1941722Notes

Reaction equation

HRID 1941722 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]=[CH:17][O:18]C)=[C:12]([F:20])[C:11]=2[F:21])=[C:6]([F:22])[C:5]=1[F:23])[CH3:2].Cl.O>CC(C)=O>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH:17]=[O:18])=[C:12]([F:20])[C:11]=2[F:21])=[C:6]([F:22])[C:5]=1[F:23])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 679922734-Ethoxy-2,2',3,3'-tetrafluoro-4'-(2-methoxyvinyl)biphenyl

Product 1

HCID 866599312-(4'-Ethoxy-2,2',3,3'-tetrafluorobiphenyl-4-yl)acetoaldehydeYield 97.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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.

Workup

  1. extractionthe water layer was extracted with toluene (100 ml) three times
  2. washThe combined organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-dcdde2e59fe347179fad14f9964efd49
Source dataset
uspto-grants-2013_03
Patent number
US08389073B2

Reaction notes

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