تفاعل #66992

معادلة التفاعل

4-hydroxy-3-methoxy-benzaldehyde

K2CO3

2-bromoethyl acetate

→

title compound

المردود 75.2%

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

المردود 75.2%

المذيبات

acetone

diethyl ether

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةis refluxed for 48 h before it
2. 2
   غسيلwashed with water (2×200 mL)
3. 3
   استخلاصThe washings are extracted with diethyl ether (200 mL)
4. 4
   تجفيفThe combined organic extracts are dried over MgSO4
5. 5
   تركيزconcentrated
6. 6
   أخرىThe remaining residue is purified by column chromatography on silica gel eluting with heptane/EA 1:1

الإجراء التجريبي

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).

المصدر