Water → 4-(3-TrifluoroMethyl-phenyl)-butyric acid

HRID 2092151Notes

Reaction equation

HRID 2092151 reaction equation
[OH-:1].[Na+].[F:3][C:4]([F:13])([F:12])[C:5]1[CH:6]=[C:7](O)[CH:8]=[CH:9][CH:10]=1.[OH2:14]>>[F:3][C:4]([F:13])([F:12])[C:5]1[CH:6]=[C:7]([CH2:4][CH2:5][CH2:10][C:9]([OH:14])=[O:1])[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 962WaterHCID 73763-(Trifluoromethyl)phenolHCID 14798Sodium Hydroxide2×

Product 1

HCID 223941944-(3-TrifluoroMethyl-phenyl)-butyric acid

Procedure

To a solution of sodium hydroxide (4.0 g, 100 mmol) in water (50 mL) was added 3-trifluoromethyl-phenol (5.4 g, 33.4 mmol) and the mixture was refluxed for 6 hrs. The pH of the solution was kept at about 10 by adding more of aqueous sodium hydroxide. The mixture was cooled to ambient temperature and extracted with ethyl acetate. The aqueous layer was treated with 3N HCl and extracted with ethyl acetate. The combined organic layers was concentrated to obtain 2.5 g of the title compound, which was used directly in the next step. 1H NMR (300 MHz, d6-DMSO) δ 12.40 (broad s, 1H), 7.51 (t, J 7.5 Hz, 1H), 7.24 (m, 3H), 4.23 (t, J 6.0 Hz, 2H), 2.71 (t, J 6.0 Hz, 2H).

Workup

  1. temperaturethe mixture was refluxed for 6 hrs
  2. extractionextracted with ethyl acetate
  3. additionThe aqueous layer was treated with 3N HCl
  4. extractionextracted with ethyl acetate
  5. concentrationThe combined organic layers was concentrated

Sources & evidence

ORD record
ord-d316060f213449b1a73ac878864057a7
Source dataset
uspto-grants-2013_05
Patent number
US08440691B2

Reaction notes

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