Water → (2R)-chloro-3-phenylpropionic acid

Temperature

40 °C

Thionyl chloride (0.66 ml, 9.0 mmol) was added dropwise to a solution of (2S)-2-hydroxy-3-phenylpropionic acid (500 mg, 3.0 mmol, optical purity 100% ee (S)) in 5 ml of tetrahydrofuran at room temperature, and the mixture was stirred for 15 hours. To the reaction mixture was added 170 mg (0.60 mmol) of tetra-n-butylammonium chloride, and the mixture was heated at 40° C. for 4 hours. Water (5 ml) was added to the reaction mixture and, after 30 minutes of stirring, the mixture was extracted with 90 ml of ethyl acetate. The organic phase was washed with 10 ml of a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give 499 mg (yield 90%) of the desired (2R)-chloro-3-phenylpropionic acid.

1. stirringof stirring
2. extractionthe mixture was extracted with 90 ml of ethyl acetate
3. washThe organic phase was washed with 10 ml of a saturated aqueous solution of sodium chloride
4. dry with materialdried over anhydrous sodium sulfate
5. distillationThe solvent was distilled off under reduced pressure

ORD record

ord-f826208111eb48df98d017f97031333a

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07094926B2