3-(Trifluoromethyl)phenol → 3-[3-(Trifluoromethyl)phenoxy]propanoic acid
Reaction equation
Cl[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[OH:7][C:8]1[CH:9]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:12][CH:13]=1>[OH-].[Na+]>[F:15][C:14]([F:16])([F:17])[C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[O:7][CH2:2][CH2:3][C:4]([OH:6])=[O:5]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- temperatureThe reaction mixture was refluxed for one hour while the pH
- washwas then washed with diethyl ether
- additionSubsequently, 1 N hydrochloric acid was added
- extractionThe reaction mixture was extracted with ethyl acetate
- washThe organic layer was sequentially washed with water
- dry with materiala saturated brine and then dried over anhydrous sodium sulfate
- distillationThe solvent was distilled off under reduced pressure, and n-hexane
- additionwas then added to the residue
- customcrystallization
Sources & evidence
- ORD record
- ord-6388d205f4b44df2a210687535578fd3
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07910751B2
Reaction notes
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