Reaktion #66989

Reaktionsgleichung

3-chloro-4-hydroxybenzaldehyde

K2CO3

2-bromoethyl acetate

→

title compound

Ausbeute 41.5%

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

Ausbeute 41.5%

Lösungsmittel

acetone

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturis refluxed for 18 h before it
2. 2
   Waschenwashed with water (3×200 mL)
3. 3
   ExtraktionThe washings are extracted with diethyl ether (200 mL)
4. 4
   TrocknenThe combined organic extracts are dried over MgSO4
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe remaining residue is purified by column chromatography on silica gel eluting with heptane/EA 1:1

Vorschrift

A mixture of 3-chloro-4-hydroxybenzaldehyde (10 g, 63.9 mmol), K2CO3 (26.5 g, 191.6 mmol) and 2-bromoethyl acetate (26.7 g, 159.7 mmol) in acetone (250 mL) is refluxed for 18 h before it is diluted with diethyl ether (200 mL) and washed with water (3×200 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 (6.44 g) as colourless solid. 1H NMR (CDCl3): δ 9.85 (s, 1H9, 7.91 (d, J=1.8 Hz, 1H), 7.75 (dd, J=1.8, 8.2 Hz, 1H), 7.03 (d, J=8.8 Hz, 1H), 4.53-4.49 (m, 2H), 4.35-4.31 (m, 2H), 2.12 (s, 3H).

Quelle