Potassium Carbonate → 2-Nitro-5-(3-tert-butylphenoxy)-p-xylene

HRID 2121832Notes

Reaction equation

HRID 2121832 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[C:19]1[CH:24]=[C:23]([CH3:25])[C:22]([N+:26]([O-:28])=[O:27])=[CH:21][C:20]=1[CH3:29]>CN(C)C=O>[CH3:3][C:1]([C:5]1[CH:6]=[C:7]([O:11][C:19]2[CH:24]=[C:23]([CH3:25])[C:22]([N+:26]([O-:28])=[O:27])=[CH:21][C:20]=2[CH3:29])[CH:8]=[CH:9][CH:10]=1)([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11450Phenol, 3-(1,1-dimethylethyl)-HCID 2527931-Chloro-2,5-dimethyl-4-nitrobenzene

Product 1

HCID 234343612-Nitro-5-(3-tert-butylphenoxy)-p-xylene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-t-Butylphenol (7.5 g) and potassium carbonate (6.9 g) are added to a solution of 1-chloro-2,5-dimethyl-4-nitrobenzene (9.5 g) in dimethylformamide (60 ml) under an inert atmosphere. The reaction mixture obtained is refluxed for 5 h and then partitioned in a water/diisopropyl ether mixture. The organic phase is washed with a basic aqueous solution and then with water at pH 7. Drying over magnesium sulphate and then addition of carbon black, followed by filtration through Celite gives, after concentration, the title product.

Workup

  1. customThe reaction mixture obtained
  2. temperatureis refluxed for 5 h
  3. custompartitioned in a water/diisopropyl ether mixture
  4. washThe organic phase is washed with a basic aqueous solution
  5. dry with materialDrying over magnesium sulphate
  6. additionaddition of carbon black
  7. filtrationfollowed by filtration through Celite
  8. customgives
  9. concentrationafter concentration

Sources & evidence

ORD record
ord-b06005e944184e1b8509fd7054c0191c
Source dataset
uspto-grants-2004_02
Patent number
US06696487B2

Reaction notes

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