Water → HCID 18546496, compound

HRID 1596316Notes

Reaction equation

HRID 1596316 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH:14]=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[C:4]([CH3:16])[CH:3]=1.[OH2:17]>CC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([OH:17])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[C:4]([CH3:16])[CH:3]=1

Participants

4

Reactant 2

HCID 962WaterHCID 18546485HCID 18546485, compound

Product 1

HCID 18546496HCID 18546496, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2.70 g (12.6 mmol) 4′-fluoro-2′-methyl-biphenyl-2-carbaldehyde in 75 ml aceton and 25 ml H2O 3.38 g (21.4 mmol) KMnO4 were added and the mixture stirred for 20 hrs. The solvent was evaporated, the residue treated with 100 ml H2O and 100 ml CH2Cl2 and the pH of the aqueous phase was adjusted to 1 with conc. H2SO4. After filtration through Hyflo, the phases were separated and the aqueous phase washed twice with 100 ml CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/MeOH 19:1) to give 4′-fluro-2′-methyl-biphenyl-2-carboxylic acid as a colorless solid, MS (EI): 230, (M+).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue treated with 100 ml H2O and 100 ml CH2Cl2
  3. filtrationAfter filtration through Hyflo
  4. customthe phases were separated
  5. washthe aqueous phase washed twice with 100 ml CH2Cl2
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by chromatography (SiO2, CH2Cl2/MeOH 19:1)

Sources & evidence

ORD record
ord-24079c0d7b684dc7a2fddd39cbcf9707
Source dataset
uspto-grants-2001_09
Patent number
US06291465B1

Reaction notes

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