Réaction #66992

Équation de réaction

4-hydroxy-3-methoxy-benzaldehyde

K2CO3

2-bromoethyl acetate

→

title compound

Rendement 75.2%

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

Rendement 75.2%

Solvants

acetone

diethyl ether

Conditions de réaction

Traitement

1. 1
   Températureis refluxed for 48 h before it
2. 2
   Lavagewashed with water (2×200 mL)
3. 3
   ExtractionThe washings are extracted with diethyl ether (200 mL)
4. 4
   SéchageThe combined organic extracts are dried over MgSO4
5. 5
   Concentrationconcentrated
6. 6
   AutreThe remaining residue is purified by column chromatography on silica gel eluting with heptane/EA 1:1

Mode opératoire

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).

Source