Benzyl Alcohol → 3-(Benzyloxy)propanoic acid

Add sodium hydride (2.22 g, 60% dispersion in mineral oil, 55.4 mmol) in small portions to a cold (0° C.) solution of benzyl alcohol (4.0 g, 37 mmol) in toluene (100 mL). Add ethyl 3-bromopropionate (8.0 g, 44 mmol) dropwise to the mixture, allow the resulting solution to warm to room temperature and stir for 1 hour. Quench the reaction with the addition of water until all bubbling ceases. Dilute the mixture with ethyl acetate (100 mL) and extract with water (100 mL) and brine (100 mL). Dry the organic extract over Na2SO4 and remove the solvent under reduced pressure to yield the crude ester as a clear oil. Dissolve the oil in methanol (20 mL) and 6 N NaOH (20 mL), stir for 1 hour, concentrate the mixture (˜20 mL) and dilute with water (20 mL). Extract the aqueous mixture once with CH2Cl2 (40 mL). Acidify the aqueous phase with conc. HCl, extract with EtOAc (3×50 mL), and dry the combined EtOAc extracts over Na2SO4. Remove the solvent under reduced pressure to yield the title compound as a clear oil (2.28 g, 34.0%) that solidifies upon standing.

1. customQuench
2. customthe reaction
3. extractionextract with water (100 mL) and brine (100 mL)
4. customDry the
5. extractionorganic extract over Na2SO4
6. customremove the solvent under reduced pressure
7. customto yield the crude ester as a clear oil
8. concentrationconcentrate the mixture (˜20 mL)
9. additiondilute with water (20 mL)
10. extractionExtract the aqueous mixture once with CH2Cl2 (40 mL)
11. extractionextract with EtOAc (3×50 mL)
12. dry with materialdry the combined EtOAc
13. customRemove the solvent under reduced pressure

ORD record

ord-b3d32619db8c454f91c6ff0ecdea30c6

Source dataset

uspto-grants-2006_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07074799B2