Acrolein → HCID 54472015, compound

HRID 596985Notes

Reaction equation

HRID 596985 reaction equation
[C:1]([O:5][C:6](=[O:9])[CH2:7][CH3:8])(=[O:4])[CH2:2][CH3:3].[CH:10]([CH:12]=[CH2:13])=[O:11].CC1C=C(C)C=C(C)N=1>S(=O)(=O)(O)O>[C:1]([O:5][CH:6]([O:9][C:10](=[O:11])[CH2:12][CH3:13])[CH:7]=[CH2:8])(=[O:4])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 7847AcroleinHCID 79532,4,6-TrimethylpyridineHCID 31263Propionic anhydride

Product 1

HCID 54472015HCID 54472015, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a solution of 345 g (2.65 mols) propionic anhydride and 1.05 g concentrated sulfuric acid maintained at 45°-50° C was added dropwise 140 g (2.5 mols) acrolein over a period of 15 minutes. The reaction mixture was stirred for an additional 10 minutes. A 2.6 g-sample of 2,4,6-trimethyl-pyridine was then added and the reaction mixture stirred at about 25° C. for about 17 hours. The reaction mixture was then distilled through a short column to give 268 g of the product as a slightly yellow liquid, b.p. 96°-101° C (0.25 mm Hg).

Workup

  1. stirringthe reaction mixture stirred at about 25° C. for about 17 hours
  2. distillationThe reaction mixture was then distilled through a short column

Sources & evidence

ORD record
ord-93bfad40d0004d0b9c3cac0133d6909c
Source dataset
uspto-grants-1977_03
Patent number
US04012526

Reaction notes

Loading…