Acetone → Ethyl 2-furanacrylate

HRID 2166704Notes

Reaction equation

HRID 2166704 reaction equation
C(OS([O:7][CH2:8][CH3:9])(=O)=O)C.C(N(CCC)CCC)CC.[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25](=[CH2:29])C(O)=O.C[C:31](C)=[O:32]>>[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH:25]=[CH:29][C:31]([O:7][CH2:8][CH3:9])=[O:32]

Participants

5

Reactant 4

HCID 180AcetoneHCID 6163Diethyl SulfateHCID 7616TripropylamineHCID 3162592-(Furan-2-yl)prop-2-enoic acid

Product 1

HCID 95368Ethyl 2-furanacrylate

Procedure

A mixture of diethylsulphate (57.41 g) and tri-n-propylamine was added dropwise with stirring to a solution of furanylacrylic acid (34.53 g) in acetone (150 ml). When the addition was complete the mixture was refluxed for six hours. The acetone was evaporated at reduced pressure. The resultant oily residue was dissolved in ethyl acetate, washed with aqueous sodium bicarbonate solution dried (MgSO4) and the solvent evaporated to yield ethyl 3-(2-furanyl)acrylate (46.7 g) as a brown oil.

Workup

  1. additionwas added dropwise
  2. additionWhen the addition
  3. temperaturewas refluxed for six hours
  4. customThe acetone was evaporated at reduced pressure
  5. dissolutionThe resultant oily residue was dissolved in ethyl acetate
  6. washwashed with aqueous sodium bicarbonate solution
  7. dry with materialdried (MgSO4)
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-ce3accae08514795b5bf6082e31dad32
Source dataset
uspto-grants-1983_06
Patent number
US04388317

Reaction notes

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