N1-(1-Methylethyl)-1,4-benzenediamine → 2,6-Di-tert-butyl4-[(4-isopropylamino-phenylamino)-methyl]-phenol

HRID 1835632

Reaktionsgleichung

Reaktionsgleichung von HRID 1835632
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.[CH:18]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=1)([CH3:20])[CH3:19]>O1CCCC1>[C:9]([C:7]1[CH:8]=[C:3]([CH2:2][NH:28][C:25]2[CH:24]=[CH:23][C:22]([NH:21][CH:18]([CH3:20])[CH3:19])=[CH:27][CH:26]=2)[CH:4]=[C:5]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:6]=1[OH:13])([CH3:12])([CH3:11])[CH3:10]

Komponenten

4

Edukt 2

HCID 85306N1-(1-Methylethyl)-1,4-benzenediamine2×HCID 612973Phenol, 4-(bromomethyl)-2,6-bis(1,1-dimethylethyl)-2×

Produkt 1

HCID 121356902,6-Di-tert-butyl4-[(4-isopropylamino-phenylamino)-methyl]-phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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 N-Isopropyl-benzene-1,4-diamine (2.40 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-bottomed flask containing solution of 4-Bromomethyl-2,6di-tert-butyl-phenol was kept in oil-bath at 85° C. Solution in the flask was continuously stirred with the help of magnetic stirrer. N-Isopropyl-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 2,6di-tert-butyl4-[(4isopropylamino-phenylamino)methyl]-phenol is 2.025 g (68%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-19df64c4f2e847bf9d644f7c8d2acb77
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06770785B1

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