反応 #51876

反応方程式

1,3-cyclohexanedione

benzyl alcohol

→

title compound

収率 69.6%

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

収率 69.6%

溶媒

toluene

反応条件

後処理

1. 1
   その他To a flask equipped with magnetic stirrer
2. 2
   温度The resulting solution was heated
3. 3
   温度under reflux for 2 hr
4. 4
   洗浄washed with saturated aqueous sodium carbonate solution (4×50 ml)
5. 5
   洗浄The organic layer was washed with brine (50 ml)
6. 6
   乾燥dried over magnesium sulfate
7. 7
   ろ過filtered
8. 8
   濃縮concentrated in vacuo
9. 9
   その他affording a brown oil which
10. 10
    その他crystallised
11. 11
    その他The crude crystalline material was triturated in isopropyl ether (100 ml)
12. 12
    ろ過The mixture was filtered
13. 13
    洗浄the crystalline material was washed with ice cold isopropyl ether (3×100 ml)
14. 14
    その他The resulting solid was dried overnight under reduced pressure

実験手順

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+).

出典