Реакция #66992

Уравнение реакции

4-hydroxy-3-methoxy-benzaldehyde

K2CO3

2-bromoethyl acetate

→

title compound

Выход 75.2%

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

Выход 75.2%

Растворители

acetone

diethyl ether

Условия реакции

Обработка

1. 1
   Температураis refluxed for 48 h before it
2. 2
   Промывкаwashed with water (2×200 mL)
3. 3
   ЭкстракцияThe washings are extracted with diethyl ether (200 mL)
4. 4
   СушкаThe combined organic extracts are dried over MgSO4
5. 5
   Концентрированиеconcentrated
6. 6
   ДругоеThe remaining residue is purified by column chromatography on silica gel eluting with heptane/EA 1:1

Методика

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).

Источник