Sodium Iodide → HCID 2777437, compound

HRID 637699Notes

Reaction equation

HRID 637699 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]([O:14][CH:15]([O:18][CH2:19][CH3:20])[CH2:16]Cl)[CH3:13].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O>[CH2:12]([O:14][CH:15]([O:18][CH2:19][CH3:20])[CH2:16][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1)[CH3:13]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 121282-Chloro-1,1-diethoxyethaneHCID 162713-Nitro-p-cresol

Product 1

HCID 2777437HCID 2777437, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 15.3 g (0.1 mole) of 4-methyl-3-nitrophenol, 16.8 g (0.11 mole) of chloroacetaldehyde diethyl acetal, 20.7 g (0.15 mole) of ground potassium carbonate, 4.5 g (30 mmole) of sodium iodide and 100 ml of dimethylformamide is boiled under reflux for 12 hours. The whole is subsequently filtered with suction, the residue is washed with dimethylformamide and the solution is concentrated by evaporation in vacuo. Chromatography of the residue over silica gel (methylene chloride) and subsequent distillation of the pure fractions (105°-110°/6.10-2 torr) yields 2-(4-methyl-3-nitrophenoxy)-acetaldehyde diethyl acetal in the form of a yellowish oil.

Workup

  1. temperatureunder reflux for 12 hours
  2. filtrationThe whole is subsequently filtered with suction
  3. washthe residue is washed with dimethylformamide
  4. concentrationthe solution is concentrated by evaporation in vacuo
  5. distillationChromatography of the residue over silica gel (methylene chloride) and subsequent distillation of the pure fractions (105°-110°/6.10-2 torr)

Sources & evidence

ORD record
ord-72a1a99389194b1abbf9fc27072b464a
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

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