Benzyl Alcohol → 3-(Benzyloxy)propanoic acid

In small portions, add sodium hydride (2.22 g, 60% dispersion in mineral oil, 55.4 mmol) 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), and stir for 1 hour. Concentrate the mixture (approximately 20 mL) and dilute with water (20 mL). Extract the aqueous mixture once with CH2Cl2 (40 mL). Acidify the aqueous phase with conc. HCl and extract with EtOAc (3×50 mL). 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 (approximately 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-a766d9f6940a49f19eb8ff062f5be56a

Source dataset

uspto-grants-2006_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07074799B2