N,N-Dimethylaniline → 2,2-Bis(4-dimethylaminophenyl)propionic acid

HRID 1199107Notes

Reaction equation

HRID 1199107 reaction equation
S(=O)(=O)(O)O.[CH3:6][N:7]([CH3:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:15]([OH:20])(=[O:19])[C:16]([CH3:18])=O.[OH-].[Na+]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:6][N:7]([CH3:14])[C:8]1[CH:13]=[CH:12][C:11]([C:16]([C:11]2[CH:12]=[CH:13][C:8]([N:7]([CH3:14])[CH3:6])=[CH:9][CH:10]=2)([CH3:18])[C:15]([OH:20])=[O:19])=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 949N,N-DimethylanilineHCID 1060Pyruvic AcidHCID 1118Sulfuric AcidHCID 14798Sodium Hydroxide

Product 1

HCID 142278752,2-Bis(4-dimethylaminophenyl)propionic acidYield 70%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 962WaterSolvent

Procedure

Into 40 ml of 20% aqueous solution of sulfuric acid was dissolved 20 g of N,N-dimethylaniline. To the solution were added 8.4 g of pyruvic acid and 0.2 g of p-toluenesulfonic acid and the mixture was heated with reflux for 24 hours. The reaction mixture was, after cooled, diluted with 200 ml of water and adjusted to pH 6 with addition of 20% aqueous solution of sodium hydroxide. The precipitated crystal was collected by filtration which was 18.0 g (yield 70%) of 2,2-bis(4-dimethylaminophenyl)propionic acid, having a melting point of 152°~154° C.

Workup

  1. temperaturethe mixture was heated
  2. temperaturewith reflux for 24 hours
  3. temperatureafter cooled
  4. filtrationThe precipitated crystal was collected by filtration which

Sources & evidence

ORD record
ord-5e41a95e0a544d7dbf0525ca019a0998
Source dataset
uspto-grants-1990_02
Patent number
US04898941

Reaction notes

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