Sodium Iodide → 1-(4-Chloro-3-nitrophenoxy)-2-propanone

HRID 637687Notes

Reaction equation

HRID 637687 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl[CH2:21][C:22](=[O:24])[CH3:23]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:21][C:22](=[O:24])[CH3:23])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 691274-Chloro-3-nitrophenol

Product 1

HCID 202556531-(4-Chloro-3-nitrophenoxy)-2-propanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 14.2 g (82 mmole) of 4-chloro-3-nitrophenol, 12.4 g (90 mmole) of ground potassium carbonate, 8.2 g (55 mmole) of sodium iodide, 8.3 g (90 mmole) of chloroacetone and 220 ml of dimethylformamide is stirred for 3 hours at room temperature. The whole is subsequently filtered, the residue is washed with dimethylformamide, the organic phase is concentrated by evaporation in vacuo and the resulting crude product is partitioned between water and methylene chloride. The solid remaining after drying and removal of the methylene chloride is recrystallised from methylene chloride/petroleum ether. 1-(4-chloro-3-nitrophenoxy)-2-propanone is obtained having a melting point of 92°-94°.

Workup

  1. filtrationThe whole is subsequently filtered
  2. washthe residue is washed with dimethylformamide
  3. concentrationthe organic phase is concentrated by evaporation in vacuo
  4. customthe resulting crude product is partitioned between water and methylene chloride
  5. customafter drying
  6. customremoval of the methylene chloride
  7. customis recrystallised from methylene chloride/petroleum ether

Sources & evidence

ORD record
ord-94d56614d08a4b3da6b423d99ef21f2a
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

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