2-Acetylhydroquinone → HCID 66777813, compound

To a solution (250 mL) of 1-(2,5-dihydroxyphenyl)ethanone (11.0 g) in acetonitrile were added 2-methoxyethylbromide (19.6 mL) and potassium carbonate (12.0 g) at room temperature, and the mixture was heated under reflux for 15 hr. The reaction mixture was allowed to cool to room temperature and filtered through celite, and the filtrate was concentrated under reduced pressure. Saturated aqueous ammonium chloride solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10, volume ratio) to give the title object compound (7.6 g, 50%) as a pale-yellow oil.

1. temperaturethe mixture was heated
2. temperatureunder reflux for 15 hr
3. filtrationfiltered through celite
4. concentrationthe filtrate was concentrated under reduced pressure
5. additionSaturated aqueous ammonium chloride solution was added to the residue
6. extractionthe mixture was extracted with ethyl acetate
7. washThe extract was washed with saturated brine
8. dry with materialdried over magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10, volume ratio)

ORD record

ord-649954b39a044b45b744189d910d7eaf

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436043B2