Benzyl Alcohol → 3-Benzyloxy-2-cyclohexen-1-one

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+).

1. customTo a flask equipped with magnetic stirrer
2. temperatureThe resulting solution was heated
3. temperatureunder reflux for 2 hr
4. washwashed with saturated aqueous sodium carbonate solution (4×50 ml)
5. washThe organic layer was washed with brine (50 ml)
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customaffording a brown oil which
10. customcrystallised
11. customThe crude crystalline material was triturated in isopropyl ether (100 ml)
12. filtrationThe mixture was filtered
13. washthe crystalline material was washed with ice cold isopropyl ether (3×100 ml)
14. customThe resulting solid was dried overnight under reduced pressure

ORD record

ord-b7ef3049764b4077ba592e53e4711e46

Source dataset

uspto-grants-2005_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06852747B2