Ethyl 2-(4-fluorophenoxy)acetate → 2-(4-Fluorophenoxy)ethanol

Temperature

0 °C

Ethyl 2-(4-fluorophenoxy)acetate (3.12 g, 15.74 mmol) was dissolved in diethyl ether (50 ml) and cooled to about 0° C. Lithium aluminum hydride (1.792 g, 47.2 mmol) was added in portions while maintaining reaction temperature below 35° C. The reaction was allowed to stir at room temperature for one hour. The crude reaction was diluted with ether (50 mL) then cooled in an ice bath and quenched by dropwise addition of water (6.1 mL), then 2 M NaOH (12.2 mL), then water (6.1 mL). The mixture was filtered and concentrated. The crude product was purified on silica gel (4:1 heptane:EtOAc as eluant) to give 2-(4-fluoro-phenoxy)-ethanol (1.36 g, 55%).

1. temperaturewhile maintaining
2. customreaction temperature below 35° C
3. customThe crude reaction
4. temperaturethen cooled in an ice bath
5. customquenched by dropwise addition of water (6.1 mL)
6. filtrationThe mixture was filtered
7. concentrationconcentrated
8. customThe crude product was purified on silica gel (4:1 heptane:EtOAc as eluant)

ORD record

ord-27795e0f62704113bd527703014f144b

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08217027B2