Hydrochloric Acid → (S)-3-(4-(benzyloxy)phenyl)-2-hydroxypropanoic acid

A solution of (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (3.00 g, 16.47 mmol) in ethanol (50 mL) was treated with benzyl chloride (4.20 g, 33.18 mmol) and potassium carbonate (4.60 g, 33.28 mmol) and the resulting mixture heated at reflux overnight. The mixture was cooled and treated with water (50 mL), and the resulting mixture stirred for 1 h. At this time ethyl acetate was added and the mixture acidified with 1N aqueous hydrochloric acid. The layers were separated and the aqueous phase extracted with ethyl acetate (3×). The organic phases were combined and concentrated in vacuo to an approximate volume of 10 mL. The resulting mixture was filtered and the isolated solid washed with diethyl ether and dried to afford (S)-3-(4-benzyloxy-phenyl)-2-hydroxy-propionic acid (3.00 g, 67%) as a white solid.

1. temperaturethe resulting mixture heated
2. temperatureat reflux overnight
3. temperatureThe mixture was cooled
4. customThe layers were separated
5. extractionthe aqueous phase extracted with ethyl acetate (3×)
6. concentrationconcentrated in vacuo to an approximate volume of 10 mL
7. filtrationThe resulting mixture was filtered
8. washthe isolated solid washed with diethyl ether
9. customdried

ORD record

ord-7bf4264f92114a73b81e0ad85409f4ab

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07741327B2