Sodium Iodide → HCID 54419692, compound

HRID 1598630Notes

Reaction equation

HRID 1598630 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[CH:14][O:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11].[I-:17].[Na+]>CC(C)=O>[I:17][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[CH:14][O:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 533948403-Methoxy-2-(2-(chloromethyl)phenyl)acrylic acid methyl ester

Product 1

HCID 54419692HCID 54419692, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of methyl 2-[2-(chloromethyl)phenyl]-3-methoxypropenoate (1.0 equiv) and sodium iodide (1.5 equiv) in acetone was stirred at room temperature and monitored to completion by GC. The resulting mixture was filtered, concentrated under vacuum, then diluted with chloroform and filtered again to remove the remaining sodium salts. The filtrate was concentrated and purified by chromatography over silica gel eluted with ethyl acetate hexane mixtures to afford methyl 2-[2-(iodomethyl)phenyl]-3-methoxypropenoate as a yellow solid.

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationconcentrated under vacuum
  3. additiondiluted with chloroform
  4. filtrationfiltered again
  5. customto remove the remaining sodium salts
  6. concentrationThe filtrate was concentrated
  7. custompurified by chromatography over silica gel
  8. washeluted with ethyl acetate hexane mixtures

Sources & evidence

ORD record
ord-56b27b99874d49bbafc6df78d7dd5762
Source dataset
uspto-grants-1998_04
Patent number
US05739140

Reaction notes

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