Reacción #342033

Ecuación de reacción

4-hydroxy-3-methyl-benzaldehyde

K2CO3

2-bromoethyl acetate

→

title compound

Rendimiento 97.5%

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

Rendimiento 97.5%

Disolventes

acetone

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturais refluxed for 18 h before it
2. 2
   Lavadowashed with water (3×250 mL)
3. 3
   ExtracciónThe washings are extracted with diethyl ether (200 mL)
4. 4
   SecadoThe combined organic extracts are dried over MgSO4
5. 5
   Concentraciónconcentrated
6. 6
   OtroThe remaining residue is purified by column chromatography on silica gel eluting with heptane/EA 1:1

Procedimiento

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).

Fuente