2,6-Ditert-butyl-4-(4-nitrophenyl)phenol → 4'-Amino-3,5-di-t-butyl-4-hydroxybiphenyl

HRID 426955Notes

Reaction equation

HRID 426955 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[CH:8]=[C:7]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:6]=1[OH:24])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].C(OCC)(=O)C>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[CH:10]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:6]([OH:24])=[C:7]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:8]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 17349052,6-Ditert-butyl-4-(4-nitrophenyl)phenolHCID 178418361HCID 178418361, compound

Product 1

HCID 155988104'-Amino-3,5-di-t-butyl-4-hydroxybiphenyl

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 50 g. (0.152 mole) of 2,6-di(t-butyl)-4-(4'-nitrophenyl)phenol in 350 ml. of ethyl acetate is reduced with hydrogen gas at about 45 psig in a Paar apparatus using 10 percent palladium on charcoal as catalyst. The mixture is allowed to stand for about 16 hours, filtered, and the filtrate evaporated under vacuum. The residue is cooled, dissolved in ethanol and triturated with water. The resulting off-white solid is recrystallized from petroleum ether to provide 4-(4'-aminophenyl)-2,6-di(t-butyl)phenol, m.p. 113°-114.5° C.

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated under vacuum
  3. temperatureThe residue is cooled
  4. dissolutiondissolved in ethanol
  5. customtriturated with water
  6. customThe resulting off-white solid is recrystallized from petroleum ether

Sources & evidence

ORD record
ord-02d86080600043bd9610765086159424
Source dataset
uspto-grants-1979_10
Patent number
US04172151

Reaction notes

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