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

HRID 432867Notes

Reaction equation

HRID 432867 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=1)([CH3:6])([CH3:5])[CH3:4].Cl[C:15]1[CH:16]=[C:17]([CH3:25])[C:18]([N+:22]([O-:24])=[O:23])=[CH:19][C:20]=1[CH3:21].O>CN1CCCC1=O>[N+:22]([C:18]1[CH:19]=[C:20]([CH3:21])[C:15]([O:13][C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([C:3]([CH3:6])([CH3:4])[CH3:5])[CH:8]=2)=[CH:16][C:17]=1[CH3:25])([O-:24])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 11450Phenol, 3-(1,1-dimethylethyl)-HCID 24758Sodium hydrideHCID 2527931-Chloro-2,5-dimethyl-4-nitrobenzene

Product 1

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

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of sodium hydride (0.4 g of 60% in oil) in dry N-methylpyrrolidinone (10 ml) was slowly added 3-tert-butylphenol (1.62 g). When effervescence had ceased, 3-chloro-6-nitro-p-xylene (1.85 g) was added and the mixture stirred at 120-40° C. for 5 hours. On cooling, the mixture was poured into water and the mixture extracted with diethyl ether (×3). The combined ether extracts were dried over magnesium sulphate, filtered and evaporated to give the title compound as a solid.

Workup

  1. temperatureOn cooling
  2. extractionthe mixture extracted with diethyl ether (×3)
  3. dry with materialThe combined ether extracts were dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-6e54497b54564f6787292a7f124fe489
Source dataset
uspto-grants-2003_12
Patent number
US06664295B2

Reaction notes

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