Ethanol → 3-Phenyloxolan-2-one

Temperature

50 °C

A suspension of potassium tert-butoxide (12.3 g) in toluene (200 mL) was treated dropwise with a mixture of phenylacetonitrile (12.9 g) and (2-bromoethoxy)trimethyl-silane (23.8 g) at room temperature. Upon completion of the addition, the reaction mixture was refluxed for 5 h, then cooled to room temperature and quenched by pouring onto a mixture of ice and water. The formed organic phase was separated and the aqueous phase was extracted with benzene. The combined organic phases were washed with water, dried over magnesium sulfate, filtered and concentrated on a rotary evaporator to give 2-phenyl-4-trimethylsilanyloxy-butyronitrile. The obtained butyronitrile derivative was redissolved in a mixture of ethanol (40 mL) and 70% aqueous sulfuric acid (40 mL), stirred at 50° C. for 3 h and, after cooling to room temperature, diluted with water (150 mL). The resulted organic phase was separated and the aqueous phase was extracted with benzene. The combined organic phases were washed with water, then with saturated aqueous solution of sodium bicarbonate, dried over magnesium sulfate, filtered, concentrated on a rotary evaporator and distilled in vacuum to give 11.0 g (62%) of the title compound.

1. temperatureafter cooling to room temperature
2. customThe resulted organic phase was separated
3. extractionthe aqueous phase was extracted with benzene
4. washThe combined organic phases were washed with water
5. dry with materialwith saturated aqueous solution of sodium bicarbonate, dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated on a rotary evaporator
8. distillationdistilled in vacuum

ORD record

ord-fd728375aa3941f69a467ee10713aa2a

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07674741B2