Hydrochloric Acid → 4-(2-Aminostyryl)-2,6-di-tert-butylphenol

HRID 53856Notes

Reaction equation

HRID 53856 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].O.Cl>CO.[Fe]>[NH2:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH:12]=[CH: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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 541417492,6-Di-tert-butyl-4-(2-nitrostyryl)phenol

Product 1

HCID 538979614-(2-Aminostyryl)-2,6-di-tert-butylphenolYield 70%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2,6-di-tert-butyl-4-(2-nitrostyryl)phenol (1.1 g, 3.1 mmol) in methanol (15 ml) was added water (4 ml), conc. hydrochloric acid (0.2 ml) and iron powder (1.7 g, 30 mmol) and the mixture was heated under reflux for 5 hrs. After filtration, followed by extraction with ethyl acetate and water, the extract was washed with water, dried over MgSO4 and concentrated. Purification of the residue by a silica gel column chromatography followed by recrystallization from hexane afforded 4-(2-aminostyryl)-2,6-di-tert-butylphenol (0.70 g, 70%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hrs
  3. filtrationAfter filtration
  4. extractionfollowed by extraction with ethyl acetate and water
  5. washthe extract was washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customPurification of the residue by a silica gel column chromatography
  9. customfollowed by recrystallization from hexane

Sources & evidence

ORD record
ord-ae5301eccfab4fa09db4a1c0eb34ddde
Source dataset
uspto-grants-1997_04
Patent number
US05621010

Reaction notes

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