Dimethylamine → HCID 19088224, compound

HRID 1464479Notes

Reaction equation

HRID 1464479 reaction equation
[CH3:1][C:2]([CH3:7])([CH2:5][OH:6])[CH:3]=O.[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[OH:16].CNC.[H][H]>[Ni].CO.O>[CH3:8][C:9]1[C:10]([OH:16])=[C:11]([CH2:3][C:2]([CH3:1])([CH3:7])[CH2:5][OH:6])[CH:12]=[C:13]([CH3:15])[CH:14]=1

Participants

8

Reactant 4

HCID 674DimethylamineHCID 77712,4-DimethylphenolHCID 116993-Hydroxy-2,2-dimethylpropionaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 19088224HCID 19088224, compoundYield 60%

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), 109 g (0.9 mol) of 2,4-dimethylphenol, 24 g (0.22 mol) of 40% strength aqueous dimethylamine and 700 g of methanol are reacted in a stirred autoclave under autogenous pressure of 20-30 bar at 160° C. for 20 h and then at 180° C. for 20 h. After the autoclave has cooled and the pressure has been released, 95 g of Raney Ni (0.1 parts based on complete mixture) are added to the reaction mixture and hydrogenation is carried out at 140° C. under 80 bar of hydrogen for 20 h. After filtration and removal of volatiles by distillation, the residue is recrystallized from methanol/water 10:3. 112 g (60%) of 3-(3,5-dimethyl-2-hydroxyphenyl)-2,2-dimethylpropanol are obtained (melting point 117° C.).

Workup

  1. customare reacted in a stirred autoclave under autogenous pressure of 20-30 bar at 160° C. for 20 h
  2. temperatureAfter the autoclave has cooled
  3. filtrationAfter filtration and removal of volatiles
  4. distillationby distillation
  5. customthe residue is recrystallized from methanol/water 10:3

Sources & evidence

ORD record
ord-420924ca863743838c3f94b346ccd7ce
Source dataset
uspto-grants-1994_04
Patent number
US05304685

Reaction notes

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