Hydrochloric Acid → 3-[3-(Trifluoromethyl)phenoxy]propanoic acid
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
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
- stirringthe solution was stirred at room temperature for 2.5 hours
- extractionThe solution 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-59642f11c649458e83ef1e27c0ed5c02
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383839B2
Reaction notes
Loading…