Water → 5-Acetyl-2-{[2-(iodomethyl)-2-propenyl]oxy}benzaldehyde

반응식

[I-:1].[Na+].[C:3]([C:6]1[CH:7]=[CH:8][C:9]([O:14][CH2:15][C:16]([CH2:18]Cl)=[CH2:17])=[C:10]([CH:13]=1)[CH:11]=[O:12])(=[O:5])[CH3:4].O>CC(C)=O>[C:3]([C:6]1[CH:7]=[CH:8][C:9]([O:14][CH2:15][C:16]([CH2:18][I:1])=[CH2:17])=[C:10]([CH:13]=1)[CH:11]=[O:12])(=[O:5])[CH3:4]

참가 물질

실험 절차

531 mg (3.54 mmol) of sodium iodide are added to 894 mg (3.54 mmol) of 5-acetyl-2-{[2-(chloromethyl)-2-propenyl]oxy}benzaldehyde in solution in 10 ml of distilled acetone. The medium is brought to reflux and is stirred for 5 hours. Water is added and then the solution is concentrated. After the addition of water and dichloromethane, the phases are separated by settling and then the aqueous phase is extracted with dichloromethane. The combined organic phases are washed, dried and then concentrated under vacuum to give 1.22 g (100%) of 5-acetyl-2-{[2-(iodomethyl)-2-propenyl]oxy}benzaldehyde in the form of a white solid which turns yellow in air; 1H NMR (300 MHz, CDCl3): 10.46 (s, 1H), 8.34 (d, J=2.4 Hz, 1H), 8.15 (dd, J=2.4 Hz and 8.7 Hz, 1H), 7.08 (d, J=8.7 Hz, 1H), 5.52 and 5.32 (2s, 2H), 4.86 (s, 2H), 4.01 (s, 2H), 2.54 (s, 3H).