反応 #51879

反応方程式

pyridinium

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

water

→

title compound

収率 100.0%

4-(2,4-Dihydroxyphenyl)cyclohexanone

収率 100.0%

溶媒

acetone

acetone

反応条件

後処理

1. 1
   その他A flask equipped with magnetic stirrer
2. 2
   温度the reaction mixture was then heated
3. 3
   温度under reflux for 8 hr
4. 4
   その他was removed in vacuo
5. 5
   その他the remaining mixture was partitioned between ethyl acetate (200 ml) and water (50 ml)
6. 6
   抽出The aqueous layer was extracted with ethyl acetate (3×50 ml)
7. 7
   洗浄the combined organic layers were washed with brine (30 ml)
8. 8
   乾燥dried (MgSO4)
9. 9
   ろ過filtered
10. 10
    濃縮concentrated under reduced pressure
11. 11
    その他to afford an off-white powder
12. 12
    洗浄After washing the powder
13. 13
    その他with dichloromethane (100 ml) and removal of excess solvent under reduced pressure

実験手順

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+).

出典