Acrylic Acid → HCID 20085357, compound

HRID 1608786Notes

Reaction equation

HRID 1608786 reaction equation
[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:2][CH3:3].[C:11]([OH:15])(=[O:14])[CH:12]=[CH2:13].[OH-].[Na+]>O>[C:5]1([N:4]([CH2:13][CH2:12][C:11]([OH:15])=[O:14])[CH2:1][CH2:2][CH3:3])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6581Acrylic AcidHCID 12153Benzenamine, N-propyl-HCID 14798Sodium Hydroxide

Product 1

HCID 20085357HCID 20085357, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-propyl aniline (5.0 g), acrylic acid (5.1 ml) and water (7 ml) was stirred for 2 hours under reflux. After cooling to room temperature, the aqueous solution was adjusted to pH 11 with 5N aqueous sodium hydroxide and washed four times with ether. The aqueous layer was acidified to pH 3 with concentrated hydrochloric acid and extracted three times with ethyl acetate. The combined organic layer was washed with saturated sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 7.2 g (94%) of the objective compound.

Workup

  1. temperatureunder reflux
  2. washwashed four times with ether
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic layer was washed with saturated sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-89ec80da4b204144a4cb351709e4cbea
Source dataset
uspto-grants-1995_03
Patent number
US05397781

Reaction notes

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