Acrylic Acid → HCID 21252814, compound

HRID 1531013Notes

Reaction equation

HRID 1531013 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]([OH:13])(=O)[CH:10]=[CH2:11].[OH-].[Na+]>O>[Cl:1][C:2]1[CH:8]=[C:7]2[C:5]3=[C:4]([C:9](=[O:13])[CH:10]=[CH:11][N:6]3[C:5]3[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][C:4]2=3)[CH:3]=1

Participants

5

Reactant 3

HCID 6581Acrylic AcidHCID 78124-ChloroanilineHCID 14798Sodium Hydroxide

Product 1

HCID 21252814HCID 21252814, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

p-chloroaniline (200 g) was suspended in water (100 ml) and acrylic acid (54.1 ml) was added to the suspension. The mixture was heated under reflux for 2 hours in a nitrogen atmosphere. After allowing to cool, 2 N aqueous solution of sodium hydroxide (500 ml) was added, and the mixture was extracted with ether. The aqueous layer was adjusted to pH 3 with 1 N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The title compound (137.3g, 87%) was obtained without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours in a nitrogen atmosphere
  3. temperatureto cool
  4. extractionthe mixture was extracted with ether
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4e5a12ef47054a5ebde3b01dd9779ee4
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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