Gamma-Butyrolactone → 4-Hydroxy-1-phenylbutan-1-one

Temperature

-78 °C

To a solution of dihydrofuran-2-one (5.71 g, 66 mmol) in diethyl ether (70 mL) at −78° C. was slowly added phenyl lithium (24 mL, 40 mmol, 1.67 M solution in cyclohexane/diethyl ether). After stirring at −78° C. for 2 hours, the reaction mixture was quenched by the addition of 10% NH4Cl (35 mL). The mixture was warmed to room temperature and the layers separated. The aqueous layer was extracted with diethyl ether (2×40 mL). The combined organics were washed with water (2×40 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (2:3 hexanes/ethyl acetate) to provide the product (6.4 g, 97%) as pale yellow oil.

1. customat −78° C.
2. customthe reaction mixture was quenched by the addition of 10% NH4Cl (35 mL)
3. temperatureThe mixture was warmed to room temperature
4. customthe layers separated
5. extractionThe aqueous layer was extracted with diethyl ether (2×40 mL)
6. washThe combined organics were washed with water (2×40 mL)
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by flash column chromatography (2:3 hexanes/ethyl acetate)

ORD record

ord-b70af7e868094773bcbf827fd7f31a11

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08236825B2