Dimethylamine → 4-(3-Hydroxy-2,2-dimethylpropyl)-2,6-dimethylphenol

HRID 1464477

Reaction equation

HRID 1464477 reaction equation
[CH3:1][C:2]([CH3:7])([CH2:5][OH:6])[CH:3]=O.[CH3:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[OH:16].CNC.[H][H]>[Ni].CO.O>[CH3:8][C:9]1[CH:14]=[C:13]([CH2:3][C:2]([CH3:1])([CH3:7])[CH2:5][OH:6])[CH:12]=[C:11]([CH3:15])[C:10]=1[OH:16]

Participants

8

Reactant 4

HCID 674DimethylamineHCID 113352,6-DimethylphenolHCID 116993-Hydroxy-2,2-dimethylpropionaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 190882134-(3-Hydroxy-2,2-dimethylpropyl)-2,6-dimethylphenolYield 92%

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 2,6-dimethylphenol, 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, 19 g of Raney Ni (0.02 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 174 g (92%) of 3-(3,5-dimethyl-4-hydroxyphenyl)-2,2-dimethylpropanol (boiling point 172°-174° C.; melting point 133°-134° 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-8e392b9e2967487bafd2fb5bc2cdb069
Source dataset
uspto-grants-1994_04
Patent number
US05304685

Linked notes

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