Potassium Hydroxide → 4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethyl-valeric acid

HRID 1698809Notes

Reaction equation

HRID 1698809 reaction equation
C([O:3][C:4](=[O:24])[C:5]([OH:23])([C:19]([F:22])([F:21])[F:20])[CH2:6][C:7]([C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[O:17][CH3:18])([CH3:9])[CH3:8])C.[OH-].[K+]>CO>[F:16][C:14]1[CH:13]=[CH:12][C:11]([O:17][CH3:18])=[C:10]([C:7]([CH3:8])([CH3:9])[CH2:6][C:5]([OH:23])([C:19]([F:22])([F:21])[F:20])[C:4]([OH:24])=[O:3])[CH:15]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 179356104-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester

Product 1

HCID 220327074-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethyl-valeric acidYield 88.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.9 g of 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethyl-valeric acid ethyl ester is refluxed with 40 ml of potassium hydroxide in methanol (10%) for 2 hours. After the solvent is concentrated by evaporation in a vacuum, water is added, it is extracted with hexane, and the separated water phase is acidified with 6N hydrochloric acid. After extraction with ethyl acetate, the ethyl acetate phase is washed with water, dried (Na2SO4) and concentrated by evaporation. The residue is crystallized from hexane. 1.55 g of 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethyl-valeric acid, melting point 102-104° C., is obtained.

Workup

  1. concentrationAfter the solvent is concentrated by evaporation in a vacuum, water
  2. additionis added
  3. extractionit is extracted with hexane
  4. extractionAfter extraction with ethyl acetate
  5. washthe ethyl acetate phase is washed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated by evaporation
  8. customThe residue is crystallized from hexane

Sources & evidence

ORD record
ord-a2780d968c704e6f89658232540bfa06
Source dataset
uspto-grants-2002_02
Patent number
US06344454B1

Reaction notes

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