Formaldehyde → 2,2'-[ethane-1,2-diylbis(iminomethanediyl)]bis(4,6-di-tert-butylphenol)

HRID 987860Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1O)([CH3:4])([CH3:3])[CH3:2].[CH2:16]([NH2:19])[CH2:17][NH2:18].[CH2:20]=[O:21].[CH3:22][OH:23]>>[C:11]([C:9]1[C:22]([OH:23])=[C:7]([CH2:8][NH:18][CH2:17][CH2:16][NH:19][CH2:6][C:7]2[CH:8]=[C:9]([C:11]([CH3:12])([CH3:13])[CH3:14])[CH:10]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:20]=2[OH:21])[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

Reactant 4

HCID 712Formaldehyde

HCID 887Methanol

HCID 3301Ethylenediamine

HCID 73112,4-Di-tert-butylphenol

Product 1

HCID 2238842,2'-[ethane-1,2-diylbis(iminomethanediyl)]bis(4,6-di-tert-butylphenol)

Procedure

A mixture of 2,4-di-tert-butylphenol (50 mmol), ethylenediamine (25 mmol) and 37% aqueous formaldehyde (50 mmol) was stirred in refluxing methanol for 2 h. The mixture was cooled to room temperature and the solid was filtered, and washed with methanol, yielding 13 in 45%. Spectroscopic data (not shown) supports formation of ligand precursor 13.

Workup

filtrationthe solid was filtered
washwashed with methanol

Sources & evidence

ORD record: ord-6f471f9f78924a098519561dc62c1d27
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06632899B2

Reaction notes

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