Sodium Iodide → HCID 17609227, compound

HRID 1169463Notes

Reaction equation

HRID 1169463 reaction equation
[O:1]=[CH:2][C:3]1[CH:12]=[CH:11][C:9]([OH:10])=[C:5]([O:6][CH2:7][CH3:8])[CH:4]=1.[CH2:13]([O:16][CH2:17][CH2:18]Cl)[CH2:14][CH3:15].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>O.CN(C=O)C>[CH2:7]([O:6][C:5]1[CH:4]=[C:3]([CH:12]=[CH:11][C:9]=1[O:10][CH2:18][CH2:17][O:16][CH2:13][CH2:14][CH3:15])[CH:2]=[O:1])[CH3:8]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8467EthylvanillinHCID 11430Potassium CarbonateHCID 1235061-(2-Chloroethoxy)propane

Product 1

HCID 17609227HCID 17609227, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of ethyl vanillin (5.0 g), 2-chloroethyl propyl ether (4.6 ml), sodium iodide (5.46 g), potassium carbonate (6.23 g) and DMF (50 ml) was stirred at 90° C. for 3 days. The reaction mixture was mixed with water and was extracted with ethyl acetate. The organic layer was washed with water and an aqueous saturated solution of sodium chloride, and was dried with magnesium sulfate. After concentration under reduced pressure, the residue was subjected to separation and purification using column chromatography (ethyl acetate:hexane 1:2) to obtain 3-ethoxy-4-(2-propoxyethoxy)benzaldehyde (7.34 g) as a light yellow, oily substance.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialan aqueous saturated solution of sodium chloride, and was dried with magnesium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. customthe residue was subjected to separation and purification

Sources & evidence

ORD record
ord-39fd4ecdc786433cb792b2c35e6f5717
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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