反应 #66992

反应方程式

4-hydroxy-3-methoxy-benzaldehyde

K2CO3

2-bromoethyl acetate

→

title compound

收率 75.2%

4-(2-acetoxy-ethoxy)-3-methoxy-benzaldehyde

收率 75.2%

溶剂

acetone

diethyl ether

反应条件

后处理

1. 1
   温度is refluxed for 48 h before it
2. 2
   洗涤washed with water (2×200 mL)
3. 3
   萃取The washings are extracted with diethyl ether (200 mL)
4. 4
   干燥The combined organic extracts are dried over MgSO4
5. 5
   浓缩concentrated
6. 6
   其他The remaining residue is purified by column chromatography on silica gel eluting with heptane/EA 1:1

实验过程

A mixture of 4-hydroxy-3-methoxy-benzaldehyde (2.5 g, 16.4 mmol), K2CO3 (6.81 g, 49.3 mmol) and 2-bromoethyl acetate (5.49 g, 32.9 mmol) in acetone (50 mL) is refluxed for 48 h before it is diluted with diethyl ether (250 mL) and washed with water (2×200 mL). The washings are extracted with diethyl ether (200 mL). The combined organic extracts are dried over MgSO4 and concentrated. The remaining residue is purified by column chromatography on silica gel eluting with heptane/EA 1:1 to afford the title compound (2.94 g) as colourless solid. 1H NMR (CDCl3):δ 9.85 (s, 1H), 7.45-7.41 (m, 2H), 6.99 (d, J=7.6 Hz, 1H), 4.51-4.47 (m, 2H), 4.34-4.30 (m, 2H), 3.94 (s, 3H), 2.11 (s, 3H).

来源