反应 #806303

反应方程式

2-hydroxy-4-methoxy-benzonitrile

potassium carbonate

iodoethane

→

2-ethoxy-4-methoxy-benzonitrile

收率 83.0%

溶剂

water

ethanol

diethyl ether

反应条件

后处理

1. 1
   温度The reaction mixture was heated
2. 2
   温度at gentle reflux for 12 h
3. 3
   其他The solvent was removed
4. 4
   其他to afford a yellow-brown paste
5. 5
   其他The layers were separated
6. 6
   萃取the aqueous layer was extracted with diethyl ether (2×150 mL)
7. 7
   洗涤The combined organic extracts were washed with water (1×20 mL), brine (1×20 mL)
8. 8
   干燥dried over anhydrous sodium sulfate
9. 9
   过滤The solids were then filtered off
10. 10
    浓缩the filtrate was concentrated in vacuo
11. 11
    其他Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32–63 μm, 60 Å silica gel)
12. 12
    洗涤eluting with 10–15% ethyl acetate in hexanes

实验过程

To a solution of 2-hydroxy-4-methoxy-benzonitrile (9.637 g, 64.61 mmol) in ethanol (50 mL) were added potassium carbonate (17.88 g, 129.2 mmol) and iodoethane (15.7 mL, 193.8 mmol). The reaction mixture was heated at gentle reflux for 12 h. The solvent was removed to afford a yellow-brown paste. It was then taken in diethyl ether (50 mL) and water (20 mL). The layers were separated and the aqueous layer was extracted with diethyl ether (2×150 mL). The combined organic extracts were washed with water (1×20 mL), brine (1×20 mL), and dried over anhydrous sodium sulfate. The solids were then filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32–63 μm, 60 Å silica gel) eluting with 10–15% ethyl acetate in hexanes yielded 2-ethoxy-4-methoxy-benzonitrile as yellow solids (9.487 g, 83%).

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