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

A round bottomed flask was charged with 4-(1,4-dioxaspiro[4.5]dec8-yl)-1,3-benzenediol (11.3 g), acetone (250 ml) and water (50 ml). To the stirred solution was added pyridinium ptoluenesulfonate (1.14 g) in one portion and the reaction mixture was then heated to reflux temperature 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 over magnesium sulfate, filtered and concentrated under reduced pressure to afford an off white powder. After washing the powder with dichloromethane (100 ml) and removing 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. temperaturethe reaction mixture was then heated
2. temperatureto reflux temperature for 8 hr
3. customwas removed in vacuo
4. customthe remaining mixture was partitioned between ethyl acetate (200 ml) and water (50 ml)
5. extractionThe aqueous layer was extracted with ethyl acetate (3×50 ml)
6. washthe combined organic layers were washed with brine (30 ml)
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customto afford an off white powder
11. washAfter washing the powder with dichloromethane (100 ml)
12. customremoving excess solvent under reduced pressure

ORD record

ord-b4c8b54733db46fbbf5359a0d1894487

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06541473B2