反応 #89962

反応方程式

potassium hydroxide

Compound A1

7-Methoxy-3,4-dihydro-1H-naphthalen-2-one

methyl iodide

THF

7-Methoxy-3,4-dihydro-1H-naphthalen-2-one

→

title compound

7-Methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one

溶媒

water

反応条件

後処理

1. 1
   温度Reflux
2. 2
   温度rapidly increases
3. 3
   温度to increase
4. 4
   workup.STIRRINGstirring
5. 5
   抽出extracted twice with CPME (1.5 L)
6. 6
   洗浄The combined organic layer was washed
7. 7
   workup.DISTILLATION(distilled water 1 L×3)
8. 8
   乾燥dried over anhydrous sodium sulfate
9. 9
   濃縮concentrated under reduced pressure
10. 10
    その他The resulting crude product was recrystallized with MeOH (1 L)
11. 11
    workup.DISTILLATIONdistilled water (500 ml)

実験手順

7-Methoxy-3,4-dihydro-1H-naphthalen-2-one (Compound A1, 209 g, 1.18 mol), tetrabutylammonium hydrogen sulfate (40 g, 0.118 mol) and methyl iodide (162 g, 2.60 mol) were suspended in THF (500 ml) at room temperature. Under stirring, the mixture was added with 50% aqueous solution of potassium hydroxide (400 g) over 5 min. Reflux occurred as the inner temperature rapidly increases. Once the inner temperature stopped to increase, stirring was continued for 45 min. The reaction solution was diluted with distilled water (1 L) and extracted twice with CPME (1.5 L). The combined organic layer was washed (distilled water 1 L×3), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting crude product was recrystallized with MeOH (1 L) and distilled water (500 ml) to obtain the title compound as a colorless needle-like crystal (177 g, 73%).

出典