Reacción #51876

Ecuación de reacción

1,3-cyclohexanedione

benzyl alcohol

→

title compound

Rendimiento 69.6%

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

Rendimiento 69.6%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroTo a flask equipped with magnetic stirrer
2. 2
   TemperaturaThe resulting solution was heated
3. 3
   Temperaturaunder reflux for 2 hr
4. 4
   Lavadowashed with saturated aqueous sodium carbonate solution (4×50 ml)
5. 5
   LavadoThe organic layer was washed with brine (50 ml)
6. 6
   Secadodried over magnesium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated in vacuo
9. 9
   Otroaffording a brown oil which
10. 10
    Otrocrystallised
11. 11
    OtroThe crude crystalline material was triturated in isopropyl ether (100 ml)
12. 12
    FiltraciónThe mixture was filtered
13. 13
    Lavadothe crystalline material was washed with ice cold isopropyl ether (3×100 ml)
14. 14
    OtroThe resulting solid was dried overnight under reduced pressure

Procedimiento

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+).

Fuente