Formaldehyde → HCID 19096938, compound

HRID 486977Notes

Reaction equation

HRID 486977 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[C:25]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:24]([OH:31])=[C:23]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:22]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[CH2:36]=O>[Pd].C(O)CCC>[C:27]([C:25]1[CH:26]=[C:21]([CH2:20][CH2:19][N:18]([CH3:36])[CH2:17][CH2:16][C:7]2[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]([OH:11])=[C:9]([C:12]([CH3:13])([CH3:15])[CH3:14])[CH:8]=2)[CH:22]=[C:23]([C:32]([CH3:35])([CH3:34])[CH3:33])[C:24]=1[OH:31])([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 15250384HCID 15250384, compound

Product 1

HCID 19096938HCID 19096938, compoundYield 100.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 2631-ButanolSolvent

Procedure

Charge a suitable reaction vessel with 3.0 g (6.2 mmols) of N,N-bis[β-(3,5-di-t-butyl-4-hydroxyphenyl)ethyl]amine, 2.2 g of 37% formaldehyde (27.1 mmols), 0.6 g of 10% Pd/C, and 15 mL of n-butanol. Purge with hydrogen and shake the vessel on a Parr Series 3900 Hydrogenation Apparatus at 60 psi (0.4 MPa) hydrogen pressure and room temperature for 5 hours. Dilute the resulting slurry with 30 mL of methylene chloride, filter, and concentrate the filtrate in vacuo to give 3.1 g of N,N-bis[β-(3,5-di-t-butyl-4-hydroxyphenyl)ethyl]methylamine as a yellow oil which slowly crystallizes on standing. GC area % analysis shows the product to be 98.8% pure.

Workup

  1. customPurge with hydrogen
  2. customat 60 psi (0.4 MPa) hydrogen pressure and room temperature
  3. customfor 5 hours
  4. additionDilute the resulting slurry with 30 mL of methylene chloride
  5. filtrationfilter
  6. concentrationconcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-7aaac08432db4032941f49528d95f1a8
Source dataset
uspto-grants-1994_03
Patent number
US05292956

Reaction notes

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