Water → 4-(2,4-Dihydroxyphenyl)cyclohexanone

A flask equipped with magnetic stirrer was charged with 4-(1,4-dioxaspiro[4.5]dec-8yl)-1,3-benzenediol (11.3 g, 45.2 mmol), acetone (250 ml) and water (50 ml). To the stirred solution was added pyridinium p-toluenesulfonate (1.14 g, 4.52 mmol) in one portion and the reaction mixture was then heated under reflux for 8 hr. After allowing the reaction mixture to cool to room temperature, most of the acetone was removed in vacuo and the remaining mixture was partitioned between ethyl acetate (200 ml) and water (50 ml). The aqueous layer was extracted with ethyl acetate (3×50 ml) and the combined organic layers were washed with brine (30 ml), dried (MgSO4), filtered and concentrated under reduced pressure to afford an off-white powder. After washing the powder with dichloromethane (100 ml) and removal of excess solvent under reduced pressure, the title compound (9.30 g, 100%) was obtained as an off-white powder. m/z (ES+) 207 (M+H+).

1. customA flask equipped with magnetic stirrer
2. temperaturethe reaction mixture was then heated
3. temperatureunder reflux for 8 hr
4. customwas removed in vacuo
5. customthe remaining mixture was partitioned between ethyl acetate (200 ml) and water (50 ml)
6. extractionThe aqueous layer was extracted with ethyl acetate (3×50 ml)
7. washthe combined organic layers were washed with brine (30 ml)
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customto afford an off-white powder
12. washAfter washing the powder
13. customwith dichloromethane (100 ml) and removal of excess solvent under reduced pressure

ORD record

ord-49de91b45821474d80dc3727241bd4f5

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07282592B2