Water → Trans 4-(5-methyl-2-furyl)-4-oxo-2-butenoic Acid

HRID 2309201Notes

Reaction equation

HRID 2309201 reaction equation
[C:1]([C:4]1[O:5][C:6]([CH3:9])=[CH:7][CH:8]=1)(=[O:3])[CH3:2].O.[C:11]([O:14]CC)(=[O:13])[CH3:12]>>[CH3:9][C:6]1[O:5][C:4]([C:1](=[O:3])/[CH:2]=[CH:12]/[C:11]([OH:14])=[O:13])=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 962Water2×HCID 8857Ethyl AcetateHCID 145142-Acetyl-5-Methylfuran

Product 1

HCID 13565866Trans 4-(5-methyl-2-furyl)-4-oxo-2-butenoic Acid

Procedure

10 g of 2-acetyl 5-methyl furan (J. Am. Chem. Soc., 72 3695 (1950)), 7.4 g monohydrated glyoxylic acid and 5 cm3 water are heated to 120°-130° C. for 5 hours, while eliminating the water formed in the course of the reaction. After cooling, 60 cm3 ethyl acetate are added and extracted with a solution of sodium carbonate. The aqueous phase is acidified, extracted with ethyl acetate, dried, and concentrated to dryness. The residue is chromtographed on silica, then, the product is recrystallized in ethyl acetate. 2.2 g of the expected product are obtained. MP=159°-162° C.

Workup

  1. customformed in the course of the reaction
  2. temperatureAfter cooling
  3. extractionextracted with a solution of sodium carbonate
  4. extractionextracted with ethyl acetate
  5. customdried
  6. concentrationconcentrated to dryness
  7. customthe product is recrystallized in ethyl acetate

Sources & evidence

ORD record
ord-680575379c384a4f80d3f858c722df24
Source dataset
uspto-grants-1987_09
Patent number
US04694019

Reaction notes

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