Dimethylformamide → 2-(4-Chlorophenyl)-3-(dimethylamino)acrylaldehyde

HRID 2418643Notes

Reaction equation

HRID 2418643 reaction equation
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=O)=[CH:9][CH:8]=1.[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH3:25][N:26]([CH3:29])[CH:27]=O>>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:13](=[CH:25][N:26]([CH3:29])[CH3:27])[CH:14]=[O:16])=[CH:11][CH:12]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 15880(4-Chlorophenyl)acetic acidHCID 24813Phosphorus oxychloride

Product 1

HCID 34489722-(4-Chlorophenyl)-3-(dimethylamino)acrylaldehyde

Conditions

Temperature
70 °C

Procedure

Phosphorus oxychloride (28 ml) was added dropwise with stirring to dry dimethylformamide (38 ml) with cooling in an ice-bath to keep the temperature below 20° C. p-Chlorophenylacetic acid (17.05 g) was added, and the solution was heated to 70° C. for 6 hours and then left to stand overnight. The red solution was poured onto ice and neutralised with 40% sodium hydroxide whilst cooling in an ice/salt bath. Potassium carbonate (150 g) was added and the mixture was heated to boiling for 0.5 hour. The precipitate which formed was filtered off, washed well with water and recrystallised from carbon tetrachloride to give, as white crystals, 2-(p-chlorophenyl)-3-dimethylaminoprop-2-enal, m.p. 120° C.

Workup

  1. temperaturewith cooling in an ice-bath
  2. additionwas added
  3. waitleft
  4. temperaturewhilst cooling in an ice/salt bath
  5. temperaturethe mixture was heated
  6. waitto boiling for 0.5 hour
  7. customThe precipitate which formed
  8. filtrationwas filtered off
  9. washwashed well with water
  10. customrecrystallised from carbon tetrachloride

Sources & evidence

ORD record
ord-bd01530092304253a49e344cfa059221
Source dataset
uspto-grants-1984_09
Patent number
US04473395

Reaction notes

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