Reaktion #51879

Reaktionsgleichung

pyridinium

4-(1,4-dioxaspiro[4.5]dec-8-yl)-1,3-benzenediol

water

→

title compound

Ausbeute 100.0%

4-(2,4-Dihydroxyphenyl)cyclohexanone

Ausbeute 100.0%

Lösungsmittel

acetone

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA flask equipped with magnetic stirrer
2. 2
   Temperaturthe reaction mixture was then heated
3. 3
   Temperaturunder reflux for 8 hr
4. 4
   Sonstigewas removed in vacuo
5. 5
   Sonstigethe remaining mixture was partitioned between ethyl acetate (200 ml) and water (50 ml)
6. 6
   ExtraktionThe aqueous layer was extracted with ethyl acetate (3×50 ml)
7. 7
   Waschenthe combined organic layers were washed with brine (30 ml)
8. 8
   Trocknendried (MgSO4)
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated under reduced pressure
11. 11
    Sonstigeto afford an off-white powder
12. 12
    WaschenAfter washing the powder
13. 13
    Sonstigewith dichloromethane (100 ml) and removal of excess solvent under reduced pressure

Vorschrift

A 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 ptoluenesulfonate (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+).

Quelle