N,N-Dimethylaniline → 4-(Dimethylamino)Benzaldehyde

HRID 1249602Notes

Reaction equation

HRID 1249602 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[CH3:11][N:12]([CH3:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>>[CH3:11][N:12]([CH3:19])[C:13]1[CH:18]=[CH:17][C:16]([CH:8]=[O:9])=[CH:15][CH:14]=1

Participants

5

Reactant 4

HCID 949N,N-DimethylanilineHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychloride

Product 1

HCID 74794-(Dimethylamino)BenzaldehydeYield 89.1%

Conditions

Temperature
90 °C

Procedure

83.0 g (0.54 mole) of phosphorus oxychloride was slowly added, drop by drop, to 33.3 g (0.45 mole) of dimethylformamide under cooling with ice. After stirring for a while, 55 g (0.45 mole) of dimethylaniline was added dropwise thereto and the resulting reaction mixture was stirred at 90° C. for 2 hours. The catalyst was slowly decomposed by the addition of 200 ml of ice water and the resulting mixture was made weakly alkaline by the addition of 350 g of a 20% aqueous sodium hydroxide solution. After the mixture was cooled by allowing it to stand for a while, the precipitated 4-dimethylaminobenzaldehyde was separated by filtration, washed thoroughly with water to remove any salts and impurities, and then dried at 50° C. Thus, there was obtained 59.8 g of 4-dimethylaminobenzaldehyde (in an 89% yield based on the dimethylaniline).

Workup

  1. additionwas added dropwise
  2. customthe resulting reaction mixture
  3. temperatureAfter the mixture was cooled
  4. customthe precipitated 4-dimethylaminobenzaldehyde was separated by filtration
  5. washwashed thoroughly with water
  6. customto remove any salts and impurities
  7. customdried at 50° C

Sources & evidence

ORD record
ord-5c426cfc741545c29b1cd684c44c62fa
Source dataset
uspto-grants-1986_12
Patent number
US04632987

Reaction notes

Loading…