1-Chloro-4-nitrobenzene → 2,6-Ditert-butyl-4-(4-nitrophenyl)phenol

HRID 2250828Notes

Reaction equation

HRID 2250828 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1>CS(C)=O>[C:11]([C:7]1[CH:8]=[C:9]([C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:15])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 11430Potassium CarbonateHCID 314052,6-Di-tert-butylphenol

Product 1

HCID 17349052,6-Ditert-butyl-4-(4-nitrophenyl)phenol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

8.40 g (40.7 mmol) 2,6-di-tert-butylphenol was dissolved in 100 ml dried DMSO. 8 g (58 mmol) potassium carbonate and 8.5 g (54 mmol) p-chloronitrobenzene were added into the DMSO solution. The DMSO solution was heated to 100˜120° C. for 12 hrs with stirring. Then the reaction mixture was allowed to cool to room temperature and poured into distilled water. The aqueous solution was acidified to pH 2˜4 and yellow precipitate was collected by filtration. The yellow precipitate was washed with water and dried. The crude yield was 92%. The yellow precipitate was purified by recrystallizing in cyanomethane, mp 157˜160° C. Elemental Anal. Calcd.: C, 73.40; H, 7.64; N, 4.28. Found: C, 73.25; H, 7.58; N, 4.25%.

Workup

  1. additionpoured
  2. distillationinto distilled water
  3. filtrationwas collected by filtration
  4. washThe yellow precipitate was washed with water
  5. customdried
  6. customThe yellow precipitate was purified
  7. customby recrystallizing in cyanomethane

Sources & evidence

ORD record
ord-dc13ea0a9b9e490aa89924d7f1b074d6
Source dataset
uspto-grants-2008_01
Patent number
US07317110B2

Reaction notes

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