Potassium Hydroxide → 3-(3-Fluorophenyl)-5-methoxybenzoic acid

HRID 1771671Notes

Reaction equation

HRID 1771671 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16]([O:18][CH3:19])[CH:17]=2)[C:11]([O:13]C)=[O:12])[CH:5]=[CH:6][CH:7]=1.[OH-].[K+]>CO.C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16]([O:18][CH3:19])[CH:17]=2)[C:11]([OH:13])=[O:12])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 75488445Methyl 3-(3-fluorophenyl)-5-methoxybenzoate

Product 1

HCID 463129223-(3-Fluorophenyl)-5-methoxybenzoic acidYield 88.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(3-fluorophenyl)-5-methoxy-benzoate (3 g, 11.5 mmol, 1.0 eq) in a mixture of methanol (20 mL) and THF (20 mL) at 0° C. was added a solution of aqueous KOH (2M aqueous solution, 20 mL, 40 mmol, 3.5 eq). The reaction mixture was stirred at room temperature for 2 h. The resulting mixture was concentrated to remove the methanol and THF then poured into water and the pH adjusted to pH 3-4 by addition of 1M HCl. The precipitate that formed was collected by filtration, washed with water and dried in vacuo to give the title compound as a white solid (2.5 g, 88%).

Workup

  1. concentrationThe resulting mixture was concentrated
  2. customto remove the methanol and THF
  3. additionthen poured into water
  4. additionthe pH adjusted to pH 3-4 by addition of 1M HCl
  5. customThe precipitate that formed
  6. filtrationwas collected by filtration
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-a4be647d97f842cb9bf6ce4295890bdd
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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