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

A round bottomed flask equipped with magnetic stirrer was charged with 4-(1,4-dioxaspiro[4.5]dec-8-yl)-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 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 removal of excess solvent under reduced pressure, the desired product (9.30 g, 100%) was obtained as an off-white white powder. m/z (ES+) 207 (M+H+); δH(CD3OD) 1.84-1.97 (2H, m), 2.15-2.23 (2H, m), 2.36-2.45 (2H, m), 2.58-2.68 (2H, m), 3.39 (1H, tt), 6.26 (1H, dd), 6.34 (1H, d), 6.96 (1H, d).

1. customA round bottomed flask equipped with magnetic stirrer
2. temperaturethe reaction mixture was then heated
3. temperatureto reflux temperature 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 over magnesium sulfate
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レコード

ord-8f4b9153cc9a412eb41a59f49848f925

出典データセット

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06933319B2