2,6-Dichloroaniline → 2,4-Bis(tert-butyl)-6-[[(2,6-dichlorophenyl)imino]methyl]phenol

HRID 601093Notes

Reaction equation

HRID 601093 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([CH:15]=NC2C(Br)=CC=CC=2Br)[C:6]=1[OH:25])([CH3:4])([CH3:3])[CH3:2].[Cl:26][C:27]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[C:28]=1[NH2:29].C(C1C(O)=C(C=C(C(C)(C)C)C=1)C=O)(C)(C)C>>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([CH:15]=[N:29][C:28]2[C:27]([Cl:26])=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:34])[C:6]=1[OH:25])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 118462,6-DichloroanilineHCID 6880233,5-Di-tert-butylsalicylaldehydeHCID 1363467102,4-Bis(tert-butyl)-6-[[(2,6-dibromophenyl)imino]methyl]phenol

Product 1

HCID 1363467092,4-Bis(tert-butyl)-6-[[(2,6-dichlorophenyl)imino]methyl]phenol

Procedure

An analogous procedure was employed to that described above for the synthesis of 2,4-bis(tert-butyl)-6-[[(2,6-dibromophenyl)imino]methyl]phenol, using 2,6-dichloroaniline (1.03 g, 6.4 mmol) and 3,5-di-tert-butyl-2-hydroxybenzaldehyde (1.5 g, 6.4 mmol). The product was purified by recrystallisation from hot ethanol and the product isolated as yellow crystals. Yield 1.87 g, 77%.

Workup

  1. customThe product was purified by recrystallisation from hot ethanol
  2. customthe product isolated as yellow crystals

Sources & evidence

ORD record
ord-0bcb8b9066574d93bf13c747ff08807c
Source dataset
uspto-grants-2011_03
Patent number
US07902308B2

Reaction notes

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