Methyl 4-(5-butoxy-2,2,3,3,4,4-hexafluoropentoxy)benzoate → 4-(5-Butoxy-2,2,3,3,4,4-hexafluoropentoxy)benzoic acid

HRID 1608899Notes

Reaction equation

HRID 1608899 reaction equation
[CH2:1]([O:5][CH2:6][C:7]([F:27])([F:26])[C:8]([F:25])([F:24])[C:9]([F:23])([F:22])[CH2:10][O:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH3:4]>[OH-].[K+]>[CH2:1]([O:5][CH2:6][C:7]([F:26])([F:27])[C:8]([F:24])([F:25])[C:9]([F:22])([F:23])[CH2:10][O:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 1

HCID 20082759Methyl 4-(5-butoxy-2,2,3,3,4,4-hexafluoropentoxy)benzoate

Product 1

HCID 200827564-(5-Butoxy-2,2,3,3,4,4-hexafluoropentoxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

Subsequently, the methyl 4-(5-butoxy-2,2,3,3,4,4-hexafluoropentoxy)benzoate was heated at reflux with 20 ml of 10% aqueous KOH for 2 hours. The resulting hydrolyzed carboxylate salt reaction product mixture was then cooled to room temperature and was acidified with concentrated (98%) sulfuric acid. The desired fluorinated benzoic acid precipitate was filtered from the aqueous solution and was washed twice with 10 ml aliquots of deionized water. The product was dried in a vacuum oven at 60° C. and a pressure of 0.2 mm Hg (0.2 torr). A total of 9.5 g of the desired 4-(5-butoxy-2,2,3,3,4,4-hexafluoropentoxy)benzoic acid was recovered.

Workup

  1. concentrationwith concentrated (98%) sulfuric acid
  2. filtrationThe desired fluorinated benzoic acid precipitate was filtered from the aqueous solution
  3. washwas washed twice with 10 ml aliquots of deionized water
  4. customThe product was dried in a vacuum oven at 60° C.
  5. customA total of 9.5 g of the desired 4-(5-butoxy-2,2,3,3,4,4-hexafluoropentoxy)benzoic acid was recovered

Sources & evidence

ORD record
ord-7567f8a0c6b8440395cd69dcb5947865
Source dataset
uspto-grants-1995_03
Patent number
US05399291

Reaction notes

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