Hydrochloric Acid → 2-hydroxy-4-(2,2,3,3,3-pentafluoropropoxy)benzoic Acid

HRID 733289Notes

Reaction equation

HRID 733289 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[K+].Cl>CO.O>[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][C:14]([F:19])([F:20])[C:15]([F:16])([F:17])[F:18])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 10108798Methyl 2-hydroxy-4-(2,2,3,3,3-pentafluoropropoxy)benzoate

Product 1

HCID 97958622-hydroxy-4-(2,2,3,3,3-pentafluoropropoxy)benzoic AcidYield 55%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of methyl 2-hydroxy-4-(2,2,3,3,3-pentafluoropropoxy)benzoate (obtained in example 1) (0.72 g, 2.40 mmol) in MeOH (9.7 mL), KOH (0.51 g, 86%; 7.80 mmol) dissolved in H2O (3 mL) was added and the resulting mixture was refluxed for 4 hours. The mixture was allowed to cool and MeOH was evaporated. The residue thus obtained was treated with H2O (5 mL) and the resulting solution was acidified with 6 N HCl. The white solid formed was collected by filtration, washed with cold H2O and dried in vacuo, yielding the title compound (55% yield).

Workup

  1. additionwas added
  2. temperaturethe resulting mixture was refluxed for 4 hours
  3. temperatureto cool
  4. customMeOH was evaporated
  5. customThe residue thus obtained
  6. customThe white solid formed
  7. filtrationwas collected by filtration
  8. washwashed with cold H2O
  9. customdried in vacuo

Sources & evidence

ORD record
ord-f1c78b66d88c45098f3614ed179d93a8
Source dataset
uspto-grants-2009_09
Patent number
US07589125B2

Reaction notes

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