Water → 3-Acetyl-5-Ethyldihydro-2(3H)-Furanone

HRID 620808Notes

Reaction equation

HRID 620808 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][C:6]([CH3:8])=[O:7])[CH3:2].O1[CH:12](CC)[CH2:11]1.[OH-].[Na+].O>C(O)(=O)C.C(O)C>[C:6]([CH:5]1[CH2:2][CH:1]([CH2:11][CH3:12])[O:3][C:4]1=[O:9])(=[O:7])[CH3:8]

Participants

7

Reactant 4

HCID 962WaterHCID 78341,2-Epoxybutane2×HCID 8868Ethyl Acetoacetate2×HCID 14798Sodium Hydroxide

Product 1

HCID 110518973-Acetyl-5-Ethyldihydro-2(3H)-FuranoneYield 45%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

2-acetyl-4-ethyl butyrolactone was prepared from ethylacetoacetate and 1,2-epoxybutane according to the method described in Johnson U.S. Pat. No. 2,443,827. A mixture of 40 g sodium hydroxide (1.0 mole), 270 ml water and 90 ml ethanol was cooled to 0°, stirred, and 130 g ethylacetoacetate (1.0 mole) and 72 g 1,2-epoxybutane (1.0 mole) added. Stirring was continued at 0°, and the mixture was thereafter left at 4° C. for 48 hours. The reaction mixture was neutralized with 80 ml acetic acid, extracted with toluene, washed with water, sodium bicarbonate and finally with water. The mixture was then dried (magnesium sulfate), filtered and the solvent removed, leaving a product, bp 86°-96°-/0.1 mm, in 45% yield.

Workup

  1. temperaturewas cooled to 0°
  2. stirringStirring
  3. customwas continued at 0°
  4. extractionextracted with toluene
  5. washwashed with water, sodium bicarbonate and finally with water
  6. dry with materialThe mixture was then dried (magnesium sulfate)
  7. filtrationfiltered
  8. customthe solvent removed
  9. customleaving a product, bp 86°-96°-/0.1 mm

Sources & evidence

ORD record
ord-d292a9983997441cbb60be08acd78418
Source dataset
uspto-grants-1989_04
Patent number
US04822813

Reaction notes

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