反応 #50162

反応方程式

4-methoxyphenol

1-bromo-2-ethylhexane

→

1-methoxy-4-(2'-ethylhexyloxy)benzene

収率 43.4%

溶媒

methanol

methanol

反応条件

後処理

1. 1
   温度this mixture was heated
2. 2
   温度to reflux for 30 min
3. 3
   温度The mixture was then heated
4. 4
   温度to reflux for 18 hours
5. 5
   その他The solvent was removed in vacuo
6. 6
   workup.DISSOLUTIONthe residue dissolved in ether (200 ml)
7. 7
   洗浄washed with dilute aqueous sodium hydroxide (500 ml ) and water (500 ml )
8. 8
   乾燥dried over MgSO4
9. 9
   濃縮concentrated in vacuo again
10. 10
    workup.DISTILLATIONDistillation at 120° C./0.1 mm Hg

実験手順

Sodium metal (6.50 g, 283 mmol) was dissolved in dry methanol (100 ml) under Ar to give a 2.5M solution of sodium methoxide. A solution of 4-methoxyphenol (29.3 g, 236 mmol) in dry methanol (150 ml) was added and this mixture was heated to reflux for 30 min. After cooling to room temperature, a solution of 1-bromo-2-ethylhexane (46.5 g, 259 mmol) in dry methanol (150 ml) was added dropwise. The mixture was then heated to reflux for 18 hours. The solvent was removed in vacuo, the residue dissolved in ether (200 ml), washed with dilute aqueous sodium hydroxide (500 ml ) and water (500 ml ), dried over MgSO4 and concentrated in vacuo again. Distillation at 120° C./0.1 mm Hg afforded 24.2 g (43%) 1-methoxy-4-(2'-ethylhexyloxy)benzene.

出典