Sodium Iodide → Methyl 4-{[2-(iodomethyl)-2-propenyl]oxy}-3-formylbenzoate

HRID 1791044Notes

Reaction equation

HRID 1791044 reaction equation
[I-:1].[Na+].Cl[CH2:4][C:5](=[CH2:20])[CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]=1[CH:18]=[O:19]>CC(C)=O>[I:1][CH2:4][C:5](=[CH2:20])[CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]=1[CH:18]=[O:19]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 22042284Methyl 4-{[2-(chloromethyl)-2-propenyl]oxy}-3-formylbenzoate

Product 1

HCID 22042282Methyl 4-{[2-(iodomethyl)-2-propenyl]oxy}-3-formylbenzoateYield 91%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

375 mg (2.5 mmol) of sodium iodide are added to 560 mg (2.08 mmol) of methyl 4-{[2-(chloromethyl)-2-propenyl]oxy}-3-formylbenzoate in solution in 20 ml of acetone. The solution is brought to reflux and is stirred for 5 hours with the exclusion of light. After the usual treatments, 680 mg (91%) of methyl 4-{[2-(iodomethyl)-2-propenyl]oxy}-3-formylbenzoate are obtained in the form of a white solid which turns yellow in light; 1H NMR (300 MHz, CDCl3): 10.48 (s, 1H), 8.48 (d, J=2.4 Hz, 1H), 8.21 (dd, J=2.4 Hz and 8.7 Hz, 1H), 7.07 (d, J=8.7 Hz, 1H), 5.54 (s, 1H), 5.35 (s, 1H), 4.87 (s, 2H), 4.04 (s, 2H), 3.89 (s, 3H, m).

Workup

  1. temperatureto reflux

Sources & evidence

ORD record
ord-4013f461401d4a6c8b6775ee63a3fbac
Source dataset
uspto-grants-2006_07
Patent number
US07071340B2

Reaction notes

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