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 250 μL of a 1.6M hexane solution of n-butyl lithium. (0.4 mmol) was added. After stirring for 15 minutes, 1.8 mL of triethoxysilane (10 mmol was added, followed by 500 μL ethyl 2-phenylethanoate (3.0 mmol), and the reaction mixture was allowed to warm to room temperature. The reaction mixture bubbled vigorously. When the bubbles subsided, the reaction mixture began to warm rapidly, causing tetrahydrofuran to begin refluxing. When the mixture cooled back to room temperature, the catalyst was quenched by exposure to air until the color changed from dark brown to yellow. Next, 5 mL of tetrahydrofuran, 15 mL of EtOH, and 0.6 g of NaOH (15 mmol) were then added. After stirring for 2 hours, the mixture was added to a water/ether mixture (150 mL each), shaken vigorously, and the layers were then separated. The aqueous layer was extracted with ether (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=1:1), which afforded 300 mg (82% yield) of phenethyl alcohol.

1. addition(0.4 mmol) was added
2. temperatureto warm to room temperature
3. customThe reaction mixture bubbled vigorously
4. temperatureto warm rapidly
5. temperatureto begin refluxing
6. temperatureWhen the mixture cooled back to room temperature
7. customthe catalyst was quenched by exposure to air until the color
8. stirringAfter stirring for 2 hours
9. stirringshaken vigorously
10. customthe layers were then separated
11. extractionThe aqueous layer was extracted with ether (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=1:1), which

ORD record

ord-9428004e83db4f24ae951e889b1a2e93

Source dataset

uspto-grants-1994_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05286878