Acrolein → HCID 14631421, compound

HRID 728839Notes

Reaction equation

HRID 728839 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][N+:6]#[C-:7])[CH3:2].[CH:9]([CH:11]=[CH2:12])=[O:10]>C1C=CC=CC=1.[Cu-]=O>[CH2:1]([O:3][C:4]([CH:5]1[CH:9]([CH:11]=[CH2:12])[O:10][CH:7]=[N:6]1)=[O:8])[CH3:2]

Participants

5

Reactant 2

HCID 7847AcroleinHCID 533707Ethyl isocyanoacetate

Product 1

HCID 14631421HCID 14631421, compound

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 241BenzeneSolvent2×

Procedure

1.6 g of red copper(I) oxide are added to 200 ml of benzene. With intensivestirring, a solution of 140 g of isocyanoacetic acid ethyl ester and 84 g of freshly distilled acrolein in 200 ml of benzene are added dropwise to this suspension within a period of 10 minutes. During the course of this addition the reaction temperature is maintained between 30° and 32° by cooling with ice. When the addition is complete the mixture is maintained at 30°-32° until the exothermic reaction has subsided, and then the whole is stirred for 1 hour at room temperature. After excess copper(I) oxide has been removed by filtration, the filtrate is concentrated by evaporation in vacuo at 30°. 600 ml of ether areadded to the residue, and the whole is filtered over celite and concentrated to dryness by evaporation in vacuo. In this manner 5-vinyl-2-oxazoline-4-carboxylic acid ethyl ester is obtained in the form of a pale yellow oil, b.p. 100°-110° (5.3 Pa).

Workup

  1. additionDuring the course of this addition the reaction temperature
  2. temperatureis maintained between 30° and 32°
  3. temperatureby cooling with ice
  4. additionWhen the addition
  5. temperatureis maintained at 30°-32° until the exothermic reaction
  6. customAfter excess copper(I) oxide has been removed by filtration
  7. concentrationthe filtrate is concentrated by evaporation in vacuo at 30°
  8. filtrationthe whole is filtered over celite and
  9. concentrationconcentrated to dryness by evaporation in vacuo

Sources & evidence

ORD record
ord-e4f04939f05d4351a4b639acd5e37314
Source dataset
uspto-grants-1991_09
Patent number
US05051413

Reaction notes

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