2,6-Di-tert-butyl-4-(2-nitrostyryl)phenol → 4-(2-Aminophenethyl)-2,6-di-tert-butylphenol

HRID 53853

Reaction equation

HRID 53853 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-])=O)[CH:8]=[C:7]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:6]=1[OH:26])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[C].[Pd]>[NH2:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][CH2:11][C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:6]([OH:26])=[C:7]([C:22]([CH3:24])([CH3:23])[CH3:25])[CH:8]=1

Participants

4

Reactant 1

HCID 541417492,6-Di-tert-butyl-4-(2-nitrostyryl)phenol

Product 1

HCID 199604694-(2-Aminophenethyl)-2,6-di-tert-butylphenolYield 199.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 2,6-di-tert-butyl-4-(2-nitrostyryl)phenol (16.4 g, 23.3 mmol) in ethanol (150 ml) was added a catalytic amount of 10% palladium carbon and the suspension was subjected to catalytic reduction at room temperature at 1-2.5 atms for 8 hrs and at 40° C. for 3 hrs. After filtering the catalyst, distilling off the solvent gave 4-(2-aminophenethyl)-2,6-di-tert-butylphenol (15.1 g, 100%) as a viscous oil.

Workup

  1. filtrationAfter filtering the catalyst
  2. distillationdistilling off the solvent

Sources & evidence

ORD record
ord-7132e3607c4742b892cc59832a2db099
Source dataset
uspto-grants-1997_04
Patent number
US05621010

Linked notes

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