Sodium Iodide → HCID 18938755, compound

HRID 356579Notes

Reaction equation

HRID 356579 reaction equation
[CH3:1][O:2][CH:3]([O:14][CH3:15])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl[CH2:25][CH2:26][CH2:27][OH:28]>CN(C=O)C.C(OCC)(=O)C>[CH3:15][O:14][CH:3]([O:2][CH3:1])[C:4]1[CH:9]=[C:8]([O:10][CH2:25][CH2:26][CH2:27][OH:28])[CH:7]=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 123133-Chloro-1-propanolHCID 32847943-(Dimethoxymethyl)-4-nitrophenol

Product 1

HCID 18938755HCID 18938755, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

5-Hydroxy-2-nitrobenzaldehyde dimethyl acetal (5.33 g) is dissolved in dry DMF (50 ml), and thereto are added potassium carbonate (6.91 g), sodium iodide (7.5 g) and 3-chloropropanol (4.73 g), and the mixture is stirred at 70° C. for 22 hours. To the mixture is added ethyl acetate, and the insoluble materials are removed by filtration. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography to give 5-(3'-hydroxypropyloxy)-2-nitrobenzaldehyde dimethyl acetal (6.39 g) as a pale yellow oil.

Workup

  1. customthe insoluble materials are removed by filtration
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. customthe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bb242bafddaf46b0b4bcd1556637bb8a
Source dataset
uspto-grants-1998_11
Patent number
US05837673

Reaction notes

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