Water → 5-Acetyl-2-{[2-(iodomethyl)-2-propenyl]oxy}benzaldehyde
Reaction equation
[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]Participants
Procedure
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).
Workup
- temperatureto reflux
- concentrationthe solution is concentrated
- additionAfter the addition of water and dichloromethane
- customthe phases are separated
- extractionthe aqueous phase is extracted with dichloromethane
- washThe combined organic phases are washed
- customdried
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-74898563749d45e290e940e012a4e69f
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07071340B2
Reaction notes
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