Dimethylamine → Cgp-7930

HRID 1464478Notes

Reaction equation

HRID 1464478 reaction equation
[CH3:1][C:2]([CH3:7])([CH2:5][OH:6])[CH:3]=O.[C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:13]=1[OH:22])([CH3:11])([CH3:10])[CH3:9].CNC.[H][H]>[Ni].CO.O>[C:18]([C:14]1[CH:15]=[C:16]([CH2:3][C:2]([CH3:1])([CH3:7])[CH2:5][OH:6])[CH:17]=[C:12]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:13]=1[OH:22])([CH3:21])([CH3:20])[CH3:19]

Participants

8

Reactant 4

HCID 674DimethylamineHCID 116993-Hydroxy-2,2-dimethylpropionaldehydeHCID 314052,6-Di-tert-butylphenolHCID 178418361HCID 178418361, compound

Product 1

HCID 5024764Cgp-7930Yield 91%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

125 g (1 mol) of 80% strength aqueous 2,2-dimethyl-3-hydroxypropanal (crude mixture from the synthesis, reduced to a water content of 20% by distillation), 185 g (0.9 mol) of 2,6-di-t-butylphenol, 12 g (0.11 mol) of 40% strength aqueous dimethylamine and 700 g of methanol are reacted in a stirred autoclave at 180° C. under autogenous pressure of 20-30 bar for 10 h. After the autoclave has cooled and the pressure has been released, 28 g of Raney Ni (0.03 parts based on complete mixture) are added to the reaction mixture and hydrogenation is carried out at 80° C. under 80 bar of hydrogen for 5 h. Workup of the mixture by distillation yields 239 g (91%) of 3-(3,5-di-t-butyl-4-hydroxyphenyl)-2,2-dimethylpropanol (boiling point 142°-145° C.; melting point 84°-86° C.).

Workup

  1. customare reacted in a stirred autoclave at 180° C. under autogenous pressure of 20-30 bar for 10 h
  2. temperatureAfter the autoclave has cooled
  3. distillationWorkup of the mixture by distillation

Sources & evidence

ORD record
ord-5110f3d3be644f859bdeaf0c41148efb
Source dataset
uspto-grants-1994_04
Patent number
US05304685

Reaction notes

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