Ethyl phenylacetate → 2-Phenylethanol

Temperature

-78 °C

To a dry Schlenk tube under argon was added 50 mg of titanocene dichloride (0.2 mmol) and 2 mL of tetrahydrofuran. The slurry was cooled to -78° C. in a dry ice/acetone bath and 200 μL of a 2M ether solution of pentylmagnesium bromide (0.4 mmol) was added. After stirring for 15 minutes, 930 μL of diphenylsilane (5.0 mmol) was added and the reaction mixture was allowed to warm to 0° C. Next 637 μL of ethyl 2-phenylethanoate (4.0 mmol) was then added and the reaction mixture was allowed to warm to room temperature. After 2 hours, an additional 200 μL of diphenylsilane was added and the reaction was stirred for 1.5 hours. The catalyst was then quenched by exposure to air until the color changed from dark brown to yellow. 5 mL of tetrahydrofuran and 15 mL of 1N NaOH in MeOH solution were then added. After stirring for 2 hours, the mixture was added to a brine/hexane mixture (150 mL each), shaken vigorously, and the layers were then separated. The aqueous layer was extracted with hexane (2×50 mL), the combined organic extracts were dried over MgSO4, filtered, and concentrated by rotary evaporation. The crude product was purified by flash chromatography (ether:hexane=3:7), which afforded 397 mg (81% yield) of phenethyl alcohol.

1. temperatureto warm to 0° C
2. temperatureto warm to room temperature
3. waitAfter 2 hours
4. stirringthe reaction was stirred for 1.5 hours
5. customThe catalyst was then quenched by exposure to air until the color
6. addition5 mL of tetrahydrofuran and 15 mL of 1N NaOH in MeOH solution were then added
7. stirringAfter stirring for 2 hours
8. additionthe mixture was added to a brine/hexane mixture (150 mL each)
9. stirringshaken vigorously
10. customthe layers were then separated
11. extractionThe aqueous layer was extracted with hexane (2×50 mL)
12. dry with materialthe combined organic extracts were dried over MgSO4
13. filtrationfiltered
14. concentrationconcentrated by rotary evaporation
15. customThe crude product was purified by flash chromatography (ether:hexane=3:7), which

ORD record

ord-1f8cb0a98e0840229126307b3f1570c1

Source dataset

uspto-grants-1994_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05286878