2,6-Diisopropyl-4-(2-nitrostyryl)phenol → 4-(2-Aminophenethyl)-2,6-diisopropylphenol

HRID 53855Notes

Reaction equation

HRID 53855 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-])=O)[CH:7]=[C:6]([CH:21]([CH3:23])[CH3:22])[C:5]=1[OH:24])([CH3:3])[CH3:2]>C(O)C.[C].[Pd]>[NH2:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][CH2:10][C:8]1[CH:9]=[C:4]([CH:1]([CH3:2])[CH3:3])[C:5]([OH:24])=[C:6]([CH:21]([CH3:22])[CH3:23])[CH:7]=1

Participants

4

Reactant 1

HCID 537304662,6-Diisopropyl-4-(2-nitrostyryl)phenol

Product 1

HCID 199604774-(2-Aminophenethyl)-2,6-diisopropylphenolYield 84.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 2,6-diisopropyl-4-(2nitrostyryl)phenol (1.3 g, 4.0 mmol) in ethanol (20 ml) was added a catalytic amount of 10% palladium carbon and the suspension was subjected to catalytic reduction at 1-2.5 atms at room temperature for 7 hrs. After filtering the catalyst, distilling off the solvent gave 4-(2-aminophenethyl)-2,6-diisopropylphenol (1.0 g, 84%) as a viscous oil.

Workup

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

Sources & evidence

ORD record
ord-1c9cec788aa34fe5b1ddb25ade677bb2
Source dataset
uspto-grants-1997_04
Patent number
US05621010

Reaction notes

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