Formaldehyde → HCID 15906154, compound

HRID 987859Notes

Reaction equation

HRID 987859 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]([NH:23][CH2:24][CH2:25][NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH2:34]=[O:35].[CH3:36][OH:37]>>[C:11]([C:9]1[C:36]([OH:37])=[C:7]([CH2:8][N:23]([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:24][CH2:25][N:26]([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:34]=2[OH:35])[CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 73112,4-Di-tert-butylphenolHCID 8793Benzathine

Product 1

HCID 15906154HCID 15906154, compound

Procedure

A mixture of 2,4-di-tert-butylphenol (50 mmol), N,N′-dibenzylethylenediamine (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 resulting oil was separated from the aqueous layer which was discarded, and evaporated. The product was then precipitated with hexanes, filtered and washed with hexanes, yielding ligand precursor 9 in 40%. Spectroscopic data (not shown) supports formation of ligand precursor 9.

Workup

  1. customthe resulting oil was separated from the aqueous layer which
  2. customevaporated
  3. customThe product was then precipitated with hexanes
  4. filtrationfiltered
  5. washwashed with hexanes
  6. customyielding ligand precursor 9 in 40%

Sources & evidence

ORD record
ord-ac0dbf9ba1bd4a1aae63086e7567f893
Source dataset
uspto-grants-2003_10
Patent number
US06632899B2

Reaction notes

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