Hydrochloric Acid → 3-[3-(Trifluoromethyl)phenoxy]propanoic acid

HRID 604949Notes

Reaction equation

HRID 604949 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:8][CH:9]=1.[C:14]1(=[O:18])[O:17][CH2:16][CH2:15]1.Cl>O.CN(C)C=O>[F:13][C:10]([F:11])([F:12])[C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[O:3][CH2:16][CH2:15][C:14]([OH:18])=[O:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 2365Beta-PropiolactoneHCID 73763-(Trifluoromethyl)phenolHCID 24758Sodium hydride

Product 1

HCID 139538203-[3-(Trifluoromethyl)phenoxy]propanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (550 mg) was added to an N,N-dimethylformamide (20.0 mL) solution of 3-hydroxybenzotrifluoride (2.0 g), and the reaction mixture was stirred at room temperature for one hour. β-Propiolactone (1.0 mL) was added thereto, and the solution was stirred at room temperature for 2.5 hours. Water was then added to the solution, and the pH was adjusted to 2 with 2 N hydrochloric acid. The solution was extracted with ethyl acetate. The organic layer was sequentially washed with water and a saturated brine and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and n-hexane was then added to the residue to perform crystallization. The title compound (2.2 g) was obtained as colorless crystals.

Workup

  1. stirringthe solution was stirred at room temperature for 2.5 hours
  2. extractionThe solution was extracted with ethyl acetate
  3. washThe organic layer was sequentially washed with water
  4. dry with materiala saturated brine and then dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure, and n-hexane
  6. additionwas then added to the residue
  7. customcrystallization

Sources & evidence

ORD record
ord-4d044da58f6d4af2a23aeded84d4b3c6
Source dataset
uspto-grants-2011_03
Patent number
US07910751B2

Reaction notes

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