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

HRID 981338Notes

Reaction equation

HRID 981338 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:13]([OH:20])=[C:12]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:11]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[C:14]([C:16]([CH3:17])([CH3:18])[CH3:19])[C:13]([OH:20])=[C:12]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:11]=2)=[CH:6][CH:5]=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-hydroxybiphenylYield 105.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5.0 g (15 mmol) of 4-(4'-nitrophenyl)-2,6-di-tert-butylphenol, 0.5 g of 5% palladium on carbon, and 250 mL of absolute ethanol was hydrogenated for one hour under 50 psig of hydrogen, filtered, and concentrated to give 4.7 g (quantitative yield) of 4-(4'-aminophenyl)-2,6-di-tert-butylphenol as a foam: 1H NMR (CDCl3) 1.48 (s, 18H), 3.25 (broad s, 2H), 5.20 (broad s, 1H), 6.67 (d, 2H, J=9 Hz), 7.36 (s, 2H), 7.36 (d, 2H, J=9 Hz). This compound may also be named 3,5-bis(1,1-dimethylethyl)-4'-amino-(1,1'-biphenyl)-4-ol.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-e9ad854e655347f4b88fff68fe7080e2
Source dataset
uspto-grants-1991_02
Patent number
US04990627

Reaction notes

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