Benzene → 3-(4-Chlorophenyl)-3-methylpentan-2-one

To a solution of 2-(4-chlorophenyl)-2-methylpropionitrile (243 mg, 1.4 mmol) in benzene (1.4 mL) was added slowly at 50° C. under an atmosphere of nitrogen and with stirring to a 2.8 M solution of ethylmagnesium chloride in tetrahydrofuran (1.45 ml, 4.1 mmol). The reaction mixture was heated to reflux for 2 h, and thereafter, cooled and poured onto 10% aqueous ammonium chloride solution (4 mL). The organic layer was separated and treated with 2 N aqueous hydrochloric acid solution (1 mL). The reaction was heated to reflux for 1 h. After cooling the reaction mixture was diluted with water and extracted twice with benzene. The organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using heptane/ethyl acetate (9:1 v/v) as eluent to give the title compound (64 mg, 20%) as a pale-yellow oil.

1. temperatureThe reaction mixture was heated
2. temperatureto reflux for 2 h
3. temperaturecooled
4. customThe organic layer was separated
5. additiontreated with 2 N aqueous hydrochloric acid solution (1 mL)
6. temperatureThe reaction was heated
7. temperatureto reflux for 1 h
8. temperatureAfter cooling the reaction mixture
9. additionwas diluted with water
10. extractionextracted twice with benzene
11. washThe organic layer was washed with brine
12. dry with materialdried over sodium sulfate
13. customevaporated under reduced pressure
14. customThe residue was purified by column chromatography on silica gel

ORD record

ord-5690007e24aa4d3e9553fef0a1aba89c

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962834B2