Ethanol → 4-Biphenylacetic acid, 2'-fluoro-

HRID 1362782Notes

Reaction equation

HRID 1362782 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.C(O)C.[OH-].[K+]>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 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 12094240Methyl (2'-fluoro[1,1'-biphenyl]-4-yl)acetate

Product 1

HCID 211014-Biphenylacetic acid, 2'-fluoro-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

26.5 g (0.11 mol) of methyl (2′-fluoro[1,1′-biphenyl]4-yl)acetate are introduced into 50 ml of ethanol and, at room temperature, a solution of 12.8 g (0.19 mol) of potassium hydroxide pellets in 25 ml of water is added. The mixture is then heated under reflux for 4 h. After cooling, the crude mixture is concentrated in vacuo, and the residue is dissolved in 100 ml of water and acidified with concentrated hydrochloric acid. The precipitate is filtered off and washed several times with water, and the solid is dried. Example VI is obtained 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 in vacuo
  5. dissolutionthe residue is dissolved in 100 ml of water
  6. filtrationThe precipitate is filtered off
  7. washwashed several times with water
  8. customthe solid is dried
  9. customExample VI is obtained in the form of white crystals

Sources & evidence

ORD record
ord-5969a26d4b0746c288d1ff7443fb81b5
Source dataset
uspto-grants-2011_02
Patent number
US07883713B2

Reaction notes

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