P-Phenylenediamine → 4-[(4-Aminoanilino)methyl]-2,6-di-tert-butylphenol

HRID 1835627Notes

Reaction equation

HRID 1835627 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:6]([OH:13])=[C:5]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:4]=1.[C:18]1([NH2:25])[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=1>O1CCCC1>[NH2:24][C:21]1[CH:22]=[CH:23][C:18]([NH:25][CH2:2][C:3]2[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:6]([OH:13])=[C:5]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:4]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 7814P-Phenylenediamine2×HCID 612973Phenol, 4-(bromomethyl)-2,6-bis(1,1-dimethylethyl)-2×

Product 1

HCID 153121044-[(4-Aminoanilino)methyl]-2,6-di-tert-butylphenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Bromomethyl-2,6-di-tert-butyl-phenol (2.42 g, 0.008 mole) was dissolved in 50 mL of dry tetrahydrofuran. In a separate conical flask benzene-1,4-diamine (p-PDA) (1.728 g, 0.016 mole) was dissolved in 25 mL of tetrahydrofuran and solution was transferred to a cylindrical funnel with pressure equalizing tube. Three-necked round-bottom flask containing solution of 4-Bromomethyl-2,6-di-tert-butyl-phenol was kept in oil-bath at 85° C. Solution in the flask was continuously stirred with the help of magnetic stirrer. Benzene-1,4-diamine solution was added drop-by-drop, from funnel to the flask in acidic medium for a span of 4-5 hours till all the solution was poured out. The reaction was terminated after that and the final reaction mixture was allowed to attain room temperature. The product was purified using silica gel column chromatography. Product was identified by 1H-NMR. The yield of 4-[(4-Amino-phenylamino)-methyl]-2,6-di-tert-butyl-phenol was 2.24 g (85%).

Workup

  1. customsolution was transferred to a cylindrical funnel with pressure
  2. customwas kept in oil-bath at 85° C
  3. additionwas poured out
  4. customThe reaction was terminated after that and the final
  5. customreaction mixture
  6. customto attain room temperature
  7. customThe product was purified

Sources & evidence

ORD record
ord-26b3b5969ed6463284caec64a73f5559
Source dataset
uspto-grants-2004_08
Patent number
US06770785B1

Reaction notes

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