Reaktion #51876

Reaktionsgleichung

1,3-cyclohexanedione

benzyl alcohol

→

title compound

Ausbeute 69.6%

3(Benzyloxy)-2-cyclohexen-1-one

Ausbeute 69.6%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a flask equipped with magnetic stirrer
2. 2
   TemperaturThe resulting solution was heated
3. 3
   Temperaturunder reflux for 2 hr
4. 4
   Waschenwashed with saturated aqueous sodium carbonate solution (4×50 ml)
5. 5
   WaschenThe organic layer was washed with brine (50 ml)
6. 6
   Trocknendried over magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo
9. 9
   Sonstigeaffording a brown oil which
10. 10
    Sonstigecrystallised
11. 11
    SonstigeThe crude crystalline material was triturated in isopropyl ether (100 ml)
12. 12
    FiltrationThe mixture was filtered
13. 13
    Waschenthe crystalline material was washed with ice cold isopropyl ether (3×100 ml)
14. 14
    SonstigeThe resulting solid was dried overnight under reduced pressure

Vorschrift

To a flask equipped with magnetic stirrer and Dean Stark apparatus was added 1,3-cyclohexanedione (70.0 g, 624 mmol), toluene (500 ml), ptoluenesulfonic acid monohydrate (1.68 g, 8.83 mmol) and benzyl alcohol (65.6 g, 606 mmol). The resulting solution was heated under reflux for 2 hr. The reaction mixture was cooled to room temperature and washed with saturated aqueous sodium carbonate solution (4×50 ml). The organic layer was washed with brine (50 ml), dried over magnesium sulfate, filtered and concentrated in vacuo, affording a brown oil which crystallised upon standing. The crude crystalline material was triturated in isopropyl ether (100 ml) and stirred at 0° C. for 2 hr. The mixture was filtered and the crystalline material was washed with ice cold isopropyl ether (3×100 ml) followed by cold petroleum ether (100 ml). The resulting solid was dried overnight under reduced pressure to furnish the title compound (85.3 g, 68%). m/z (ES+) 203 (M+H+).

Quelle