Chloroselenobenzene → 2-Cyclohexen-1-one, 4-phenyl-

Under a nitrogen atmosphere, a solution of 11.0 grams (0.063 mole) of 4-phenylcyclohexanone in 400 mL of ethyl acetate was stirred, and 14.5 grams (0.076 mole) of phenylselenenyl chloride was added in one portion. The reaction mixture was stirred for one hour and then was washed with three 100 mL portions of water. Tetrahydrofuran, 200 mL, was added, and the reaction mixture was cooled in an ice-bath. The reaction mixture was stirred, and 18.1 mL (0.160 mole) of aqueous 30% hydrogen peroxide was added at a rate to maintain the reaction mixture temperature below 35° C. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature, where it was stirred for about one hour. The reaction mixture was then washed with one 100 mL portion of water and two 50 mL portions of aqueous 20% sodium carbonate. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel. Elution was accomplished commencing with 10% diethyl ether in petroleum ether and finishing with 20% diethyl ether in petroleum ether. The product-containing fractions were combined and concentrated under reduced pressure, yielding 4.6 grams of 85% pure 4-phenyl-2-cyclohexenone. The NMR spectrum was consistent with the proposed structure. This reaction was repeated on a larger scale.

1. washwas washed with three 100 mL portions of water
2. additionTetrahydrofuran, 200 mL, was added
3. temperaturethe reaction mixture was cooled in an ice-bath
4. stirringThe reaction mixture was stirred
5. addition18.1 mL (0.160 mole) of aqueous 30% hydrogen peroxide was added at a rate
6. temperatureto maintain the reaction mixture temperature below 35° C
7. additionUpon completion of addition
8. stirringwhere it was stirred for about one hour
9. washThe reaction mixture was then washed with one 100 mL portion of water and two 50 mL portions of aqueous 20% sodium carbonate
10. dry with materialThe organic layer was dried with magnesium sulfate
11. filtrationfiltered
12. concentrationThe filtrate was concentrated under reduced pressure to a residue
13. washElution
14. concentrationconcentrated under reduced pressure

ORD record

ord-fc719d058a8e43f99d847759d77229ec

Source dataset

uspto-grants-1998_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05712281