Methanol → Methyl 2-(3-methyl-4-fluorophenyl)-5-fluorobenzoic acid

HRID 1607441Notes

Reaction equation

HRID 1607441 reaction equation
[OH-].[K+].O.[CH3:4][C:5]1[CH:6]=[C:7]([C:12]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:13]=2[C:14]([O:16]C)=[O:15])[CH:8]=[CH:9][C:10]=1[F:11].[CH3:23]O>>[CH3:23][C:21]1[C:12]([C:7]2[CH:8]=[CH:9][C:10]([F:11])=[C:5]([CH3:4])[CH:6]=2)=[C:13]([CH:18]=[C:19]([F:22])[CH:20]=1)[C:14]([OH:16])=[O:15]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14797Potassium HydroxideHCID 15037296Methyl 2-(3-methyl-4-fluorophenyl)-5-fluorobenzoate

Product 1

HCID 19874639Methyl 2-(3-methyl-4-fluorophenyl)-5-fluorobenzoic acid

Procedure

Potassium hydroxide (6 g) and water (50 mL) were added to a solution of methyl 2-(3-methyl-4-fluorophenyl)-5-fluorobenzoate (10.2 g, 40.0 mmol) in methanol (150 mL) and the mixture was stirred at room temperature for 18 h. The reaction mixture was then evaporated to near dryness, acidified with 1N aqueous hydrochloric acid, and extracted with ethyl acetate. The combined extracts were washed with brine, dried over MgSO4, and concentrated to leave a residue which was chromatographed on silica gel using 30% ethyl acetate in hexane to provide 9.7 g of the acid.

Workup

  1. customThe reaction mixture was then evaporated
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto leave a residue which
  7. customwas chromatographed on silica gel using 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8ef14881d394424cbc709cac95c04387
Source dataset
uspto-grants-1989_09
Patent number
US04864028

Reaction notes

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