3-(Trifluoromethyl)phenol → 3-[3-(Trifluoromethyl)phenoxy]propanoic acid

3-Chloropropionic acid (25 g) was added dropwise to a 2 N aqueous sodium hydroxide solution (120 mL) of 3-hydroxybenzotrifluoride (25 g). The reaction mixture was refluxed for one hour while the pH was maintained at 10 or more with a 5 N aqueous sodium hydroxide solution. The reaction mixture was cooled to room temperature and was then washed with diethyl ether. Subsequently, 1 N hydrochloric acid was added thereto so that the solution became acidic. The reaction mixture 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 (6.1 g) was obtained as colorless crystals.

1. temperatureThe reaction mixture was refluxed for one hour while the pH
2. washwas then washed with diethyl ether
3. additionSubsequently, 1 N hydrochloric acid was added
4. extractionThe reaction mixture was extracted with ethyl acetate
5. washThe organic layer was sequentially washed with water
6. dry with materiala saturated brine and then dried over anhydrous sodium sulfate
7. distillationThe solvent was distilled off under reduced pressure, and n-hexane
8. additionwas then added to the residue
9. customcrystallization

ORD record

ord-8c31230fc48e4fc3b4513decb092f308

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08383839B2