Dimethylamine → Phenol

HRID 2057723Notes

Reaction equation

HRID 2057723 reaction equation
[CH3:1][NH:2][CH3:3].[C:4]1([OH:10])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:11]=[O:12]>CO>[C:4]1([OH:10])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:1][N:2]([CH2:7][C:6]1[CH:5]=[CH:4][CH:9]=[CH:8][C:11]=1[OH:12])[CH3:3]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 996Phenol

Product 2

HCID 996PhenolHCID 328972-((Dimethylamino)methyl)phenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

0.45 kg of dimethylamine was passed, under normal pressure and at a reaction temperature of 20°-25° C., in the course of 5 hours into a mixture of 1.0 kg of phenol, 0.30 kg of paraformaldehyde and 3.1 kg of methanol and the reaction mixture was then warmed to 60° C. for 1 hour. After distilling off methanol and water in vacuo, 1.551 kg of a mixture which contained 0.242 kg of phenol, 0.605 kg of o-dimethylaminomethylphenol, 0.030 kg of p-dimethylaminomethylphenol, 0.302 kg of bis- and tris-dimethylaminomethylphenol and 0.392 kg of condensation and resinification products was obtained and 0.595 kg (49% of theory, relative to converted phenol), of o-dimethylaminomethylphenol could be obtained from this mixture.

Workup

  1. distillationAfter distilling off methanol and water in vacuo, 1.551 kg of a mixture which
  2. custom0.242 kg of phenol, 0.605 kg of o-dimethylaminomethylphenol, 0.030 kg of p-dimethylaminomethylphenol, 0.302 kg of bis- and tris-dimethylaminomethylphenol and 0.392 kg of condensation
  3. customresinification products was obtained

Sources & evidence

ORD record
ord-880190c9d96d4eb9b79e2aab5dfd7012
Source dataset
uspto-grants-1980_07
Patent number
US04212822

Reaction notes

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