Citric Acid → 1-Chloro-4-methoxy-5-methyl-2-nitrobenzene

HRID 1443467Notes

Reaction equation

HRID 1443467 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([OH:11])=[C:4]([CH3:12])[CH:3]=1.[C:13](=O)([O-])[O-].[K+].[K+].CI.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([O:11][CH3:13])=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 13785667HCID 13785667, compound

Product 1

HCID 137856681-Chloro-4-methoxy-5-methyl-2-nitrobenzeneYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-chloro-2-methyl-5-nitrophenol (18.8 g, 100 mmol) in DMF (200 ml) was added potassium carbonate (13.8 g, 100 mmol) and methyl iodide (21.3 g, 150 mmol). The mixture was stirred for about two hours at room temperature. 5% Citric acid was added and the mixture was extracted three times with ethyl acetate. The organic phase was washed with brine, dried with sodium sulphate and evaporated under reduced pressure which gave the title compound (20 G, 100%).

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried with sodium sulphate
  4. customevaporated under reduced pressure which

Sources & evidence

ORD record
ord-b9ad01e20d3643a9bdf09246d02b8172
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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