反応 #167189

反応方程式

4-hydroxy-3-methyl-benzaldehyde

K2CO3

2-bromoethyl acetate

→

title compound

収率 97.5%

4-(2-acetoxy-ethoxy)-3-methylbenzaldehyde

収率 97.5%

溶媒

acetone

diethyl ether

反応条件

後処理

1. 1
   温度is refluxed for 18 h before it
2. 2
   洗浄washed with water (3×250 mL)
3. 3
   抽出The washings are extracted with diethyl ether (200 mL)
4. 4
   乾燥The combined organic extracts are dried over MgSO4
5. 5
   濃縮concentrated
6. 6
   その他The remaining residue is purified by column chromatography on silica gel eluting with heptane/EA 1:1

実験手順

A mixture of 4-hydroxy-3-methyl-benzaldehyde (7.0 g, 51.4 mmol), K2CO3 (21.32 g, 154.2 mmol) and 2-bromoethyl acetate (25.8 g, 154.2 mmol) in acetone (250 mL) is refluxed for 18 h before it is diluted with diethyl ether (300 mL) and washed with water (3×250 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 (11.14 g) as colourless solid. 1H NMR (CDCl3): δ 9.85 (s, 1H), 7.72-7.67 (m, 2H), 6.92-6.88 (m, 1H), 4.51-4.46 (m, 2H), 4.29-4.25 (m, 2H), 2.27 (s, 3H), 2.11 (s, 3H).

出典