Sodium Iodide → HCID 54127100, compound

HRID 1026784Notes

Reaction equation

HRID 1026784 reaction equation
[C:1]([O:4][CH2:5]Cl)(=[O:3])[CH3:2].[I-].[Na+].[CH:9](=[O:17])[C:10]1[C:11](=[CH:13][CH:14]=[CH:15][CH:16]=1)[OH:12].C(=O)([O-])[O-].[K+].[K+].C(OCI)(=O)C>CC(C)=O.O>[C:1]([O:4][CH2:5][O:12][C:11]1[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=1[CH:9]=[O:17])(=[O:3])[CH3:2]

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 69366Chloromethyl acetateHCID 11820084Iodomethyl acetate

Product 1

HCID 54127100HCID 54127100, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

20 g (185 mmol) of chloromethyl acetate is dissolved in acetone, to which 35 g (230 mmol) of sodium iodide is added. After stirring for 24 hours, 14.8 g (138 mmol) of salicylaldehyde and 38.20 g (276 mmol) of potassium carbonate are dissolved in 100 mL of acetone. The mixture is stirred at room temperature and freshly prepared suspension of iodomethyl acetate is added. After stirring for 24 hours at 50° C., water is added and the mixture is extracted with ethyl acetate. The organic phase is dried over magnesium sulphate, filtered and then concentrated. The residue is purified by silica gel chromatography and eluted with a heptane/ethyl acetate mixture, 7/3. 21.79 g of 2-acetoxymethoxy-benzaldehyde is obtained in the form of a yellow oil at a yield of 98%.

Workup

  1. additionis added
  2. stirringThe mixture is stirred at room temperature
  3. additionis added
  4. stirringAfter stirring for 24 hours at 50° C.
  5. extractionthe mixture is extracted with ethyl acetate
  6. dry with materialThe organic phase is dried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is purified by silica gel chromatography
  10. washeluted with a heptane/ethyl acetate mixture, 7/3

Sources & evidence

ORD record
ord-ad635c07b2604bfc9de92b23242d1264
Source dataset
uspto-grants-2014_05
Patent number
US08729312B2

Reaction notes

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