Potassium Hydroxide → 4-Biphenylacetic acid, 2'-fluoro-

HRID 2213527Notes

Reaction equation

HRID 2213527 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([O:17]C)=[O:16])=[CH:10][CH:9]=1.[OH-].[K+]>C(O)C.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 12094240Methyl (2'-fluoro[1,1'-biphenyl]-4-yl)acetate

Product 1

HCID 211014-Biphenylacetic acid, 2'-fluoro-

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

26.5 g (0.11 mol) of methyl (2′-fluoro[1,1′-biphenyl]-4-yl)acetate are initially charged in 50 ml of ethanol and, at room temperature, admixed with a solution of 12.8 g (0.19 mol) of potassium hydroxide pellets in 25 ml of water. The mixture is then heated under reflux for 4 h. After cooling, the crude mixture is concentrated under reduced pressure, and the residue is dissolved in 100 ml of water and acidified using conc. hydrochloric acid. The precipitate is filtered off and washed repeatedly with water, and the solid is dried. This gives Example VI in the form of white crystals.

Workup

  1. temperatureThe mixture is then heated
  2. temperatureunder reflux for 4 h
  3. temperatureAfter cooling
  4. concentrationthe crude mixture is concentrated under reduced pressure
  5. dissolutionthe residue is dissolved in 100 ml of water
  6. filtrationThe precipitate is filtered off
  7. washwashed repeatedly with water
  8. customthe solid is dried

Sources & evidence

ORD record
ord-b850897f2d5f40ac825df86013e01f57
Source dataset
uspto-grants-2006_09
Patent number
US07105553B2

Reaction notes

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