Sodium Iodide → 2-{[2-(Chloromethyl)-2-propenyl]oxy}benzaldehyde

HRID 1791035Notes

Reaction equation

HRID 1791035 reaction equation
[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[Cl:9][CH2:10][C:11]([CH2:13]Cl)=[CH2:12].[OH:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=[O:19]>CC(C)=O>[Cl:9][CH2:10][C:11](=[CH2:12])[CH2:13][O:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=[O:19]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 158593-Chloro-2-chloromethyl-1-propene

Product 1

HCID 112180762-{[2-(Chloromethyl)-2-propenyl]oxy}benzaldehydeYield 100.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

45 g (0.3 mol) of sodium iodide, 16.5 (0.12 mol) of potassium carbonate and 17.36 ml (0.15 mol) of 3-chloro-2-chloromethyl-1-propene are added to 10.4 ml (0.1 mol) of 2-hydroxybenzaldehyde in solution in acetone. The mixture is left at reflux of the solvent for 12 hours and then the solvent is evaporated. The medium is diluted in ether and the organic phases are subsequently washed successively with a saturated sodium sulfite solution and with brine and are then dried over magnesium sulfate. Purification by chromatography on silica gel (ethyl ether/heptane 30/70) provides 21.1 g (70%) of 2-{[2-(chloromethyl)-2-propenyl]oxy}benzaldehyde; 1H NMR (300 MHz, CDCl3): 10.46 (s, 1H), 7.82 (dd, J=8.4 and 2.4 Hz, 1H), 7.5 (dd, J=2.4 Hz and 8.4 Hz, 1H), 7.00 (m, 2H), 5.49 and 5.32 (2s, 2H), 4.78 (s, 2H), 4.01 (s, 2H).

Workup

  1. waitThe mixture is left
  2. temperatureat reflux of the solvent for 12 hours
  3. customthe solvent is evaporated
  4. additionThe medium is diluted in ether
  5. washthe organic phases are subsequently washed successively with a saturated sodium sulfite solution and with brine
  6. dry with materialare then dried over magnesium sulfate
  7. customPurification by chromatography on silica gel (ethyl ether/heptane 30/70)

Sources & evidence

ORD record
ord-141dcc1cc5a140088ea5e68d2399c500
Source dataset
uspto-grants-2006_07
Patent number
US07071340B2

Reaction notes

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