反応 #432178

反応方程式

tetrahydrofuran

1,8-dichloroanthraquinone

18-crown-6

sodium methoxide

→

1,8-dimethoxyanthraquinone

収率 50.0%

溶媒

EtOAc toluene

methanol

反応条件

後処理

1. 1
   その他A 5-liter round-bottom flask equipped with an overhead stirrer
2. 2
   温度thermocouple, and reflux condenser with a nitrogen/vacuum outlet
3. 3
   その他This solution was deoxygenated
4. 4
   温度heated until a clear solution
5. 5
   その他was obtained
6. 6
   温度The reaction mixture was heated
7. 7
   温度The reaction was cooled overnight in an ice bath
8. 8
   その他the crystallized product isolated by filtration (82% crude yield)
9. 9
   その他This material was recrystallized from 1000 mL of toluene

実験手順

A 5-liter round-bottom flask equipped with an overhead stirrer, thermocouple, and reflux condenser with a nitrogen/vacuum outlet was charged with 1200 mL of tetrahydrofuran, 138.5 grams of 1,8-dichloroanthraquinone, and 35.6 grams of 18-crown-6. This solution was deoxygenated, stirred under nitrogen, and heated until a clear solution was obtained. A solution of 165.0 grams of sodium methoxide in 1000 mL of methanol (prepared from sodium metal) was then added over a period of 30 min. The reaction mixture was heated at reflux for 24 hours, at which time TLC (silica gel, 1:1 EtOAc/toluene) indicated that the reaction was complete. The reaction was cooled overnight in an ice bath and the crystallized product isolated by filtration (82% crude yield). This material was recrystallized from 1000 mL of toluene to afford 1,8-dimethoxyanthraquinone in an overall yield of 50%.

出典