Acrylic Acid → 3-(Methylphenylamino)-propionic acid

HRID 1197405Notes

Reaction equation

HRID 1197405 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[CH3:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[C:1]([CH2:2][CH2:3][N:7]([CH3:6])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 6581Acrylic AcidHCID 7515N-MethylanilineHCID 10340Sodium Carbonate

Product 1

HCID 125224893-(Methylphenylamino)-propionic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acrylic acid (36.03 g; 0.5 mol) was added to N-methylaniline (53.58 g; 0.5 mol) and an exothermic reaction took place after which reaction was virtually complete. The mixture was stood overnight at room temperature and then diluted with water and made alkaline by the addition of sodium carbonate. The mixture was washed with dichloromethane and then the aqueous layer was cautiously acidified to pH 4.5 by the addition of concentrated hydrochloric acid SG 1.18. The resulting mixture was extracted into dichloromethane and washed with water The organic extract was dried (MgSO4) and the solvent removed by evaporation under reduced pressure to give a pale brown oil (57.32 g; 64%).

Workup

  1. customan exothermic reaction
  2. customafter which reaction
  3. washThe mixture was washed with dichloromethane
  4. additionthe aqueous layer was cautiously acidified to pH 4.5 by the addition of concentrated hydrochloric acid SG 1.18
  5. extractionThe resulting mixture was extracted into dichloromethane
  6. washwashed with water The
  7. extractionorganic extract
  8. dry with materialwas dried (MgSO4)
  9. customthe solvent removed by evaporation under reduced pressure
  10. customto give a pale brown oil (57.32 g; 64%)

Sources & evidence

ORD record
ord-d6b869fab4004ef29778c534ba84c5fb
Source dataset
uspto-grants-1994_01
Patent number
US05275924

Reaction notes

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