Sodium Iodide → 1-(4-Methyl-3-nitrophenoxy)propan-2-one

HRID 637691Notes

Reaction equation

HRID 637691 reaction equation
Cl[CH2:2][C:3](=[O:5])[CH3:4].[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[N+:14]([O-:16])=[O:15].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O>[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:2][C:3](=[O:5])[CH3:4])=[CH:9][C:8]=1[N+:14]([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 162713-Nitro-p-cresol

Product 1

HCID 202556351-(4-Methyl-3-nitrophenoxy)propan-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

40.7 g (0.44 mole) of chloroacetone are added dropwise at room temperature, with stirring, over a period of 30 minutes to a suspension of 61.25 g (0.4 mole) of 4-methyl-3-nitrophenol, 60.8 g (0.44 mole) of ground potassium carbonate, 39.9 g (0.267 mole) of sodium iodide and 900 ml of dimethylformamide. After a further 3 hours at room temperature, the whole is filtered with suction and the residue is washed with dimethylformamide. The organic solution is concentrated by evaporation in vacuo and the resulting crude product is partitioned between methylene chloride and water. The residue remaining after drying and removal of the methylene chloride is chromatographed over silica gel with petroleum ether/methylene chloride. Subsequent recrystalliation from methylene chloride/petroleum ether yields 1-(4-methyl-3-nitrophenoxy)-2-propanone having a melting point of 84°-86°.

Workup

  1. filtrationthe whole is filtered with suction
  2. washthe residue is washed with dimethylformamide
  3. concentrationThe organic solution is concentrated by evaporation in vacuo
  4. customthe resulting crude product is partitioned between methylene chloride and water
  5. customafter drying
  6. customremoval of the methylene chloride
  7. customis chromatographed over silica gel with petroleum ether/methylene chloride

Sources & evidence

ORD record
ord-5819904cc8344872a9a4d5c0d12b9b29
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

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