반응 #66989

반응 방정식

3-chloro-4-hydroxybenzaldehyde

K2CO3

2-bromoethyl acetate

→

title compound

수율 41.5%

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

수율 41.5%

용매

acetone

diethyl ether

반응 조건

후처리

1. 1
   온도is refluxed for 18 h before it
2. 2
   세척washed with water (3×200 mL)
3. 3
   추출The washings are extracted with diethyl ether (200 mL)
4. 4
   건조The combined organic extracts are dried over MgSO4
5. 5
   농축concentrated
6. 6
   기타The remaining residue is purified by column chromatography on silica gel eluting with heptane/EA 1:1

실험 절차

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).

출처