Ethyl Acetoacetate → 3-Acetyl-5-Ethyldihydro-2(3H)-Furanone

HRID 2081277Notes

Reaction equation

HRID 2081277 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].O1C=C[CH2:12][C:11]1=O>>[C:3]([CH:2]1[CH2:9][CH:8]([CH2:11][CH3:12])[O:7][C:1]1=[O:6])(=[O:4])[CH3:5]

Participants

3

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 1407652(3H)-Furanone

Product 1

HCID 110518973-Acetyl-5-Ethyldihydro-2(3H)-FuranoneYield 92.5%

Conditions

Temperature
60 °C

Procedure

The organic layer was stripped using an aspirator vacuum (60 mm) and heating the flask to 60° C. leaving a net residue of 618 g. The residue was distilled using a packed column and Perkins Triangle Head. The product obtained by distillation comprised three fractions, 164 g, 130 g, and 114 g, respectively, comprising mostly ethyl acetoacetate. The pot material was filtered and the distillation continued to obtain 16.1 g of a fourth fraction boiling below 105° C. at 5 torr that comprised 8% lactone and 887 g of a fifth fraction having a boiling point of 110-120° C. at 5 torr that comprised 92.5% of the desired product when analyzed by gas chromatography. Yield of lactone (fifth fraction) was 42%.

Workup

  1. customleaving a net residue of 618 g
  2. distillationThe residue was distilled
  3. customThe product obtained by distillation
  4. filtrationThe pot material was filtered
  5. distillationthe distillation
  6. customto obtain 16.1 g of a fourth fraction

Sources & evidence

ORD record
ord-8b3151a5d9af4ac2a295554ab057b4d2
Source dataset
uspto-grants-1993_02
Patent number
US05183908

Reaction notes

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