Acetone → 3,3-Diethylpentane-2,4-dione

HRID 1375094Notes

Reaction equation

HRID 1375094 reaction equation
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].Br[CH2:9][CH3:10].C(=O)([O-])[O-].[K+].[K+].[CH3:17][C:18](C)=O>>[CH2:17]([C:3]([CH2:9][CH3:10])([C:2](=[O:7])[CH3:1])[C:4](=[O:6])[CH3:5])[CH3:18]

Participants

5

Reactant 4

HCID 180AcetoneHCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 31261Acetylacetone

Product 1

HCID 847993,3-Diethylpentane-2,4-dione

Procedure

25 g of 2,4-pentandione, 98.3 g of bromo-ethane, 80 g of potassium carbonate, and 175 ml of acetone were mixed and refluxed for 39.5 hours. The solid was filtered off and washed with petroleum ether and acetone. To the liquid layer, 2.0 g of 1,8-diazabicyclo-[5.4.0]-undec-7-ene was added and the mixture was refluxed for two days. After addition of an additional 11.6 g of 1,8-diazabicyclo-[5.4.0]-undec-7-ene and refluxing for seven hours, 25 g of ethyl acrylate was added and the mixture was stirred at room temperature, and the solvent was distilled off and the mixture was refluxed for 8 hours. The base was neutralized by adding acetic acid, washed with an aqueous potassium carbonate solution, and extracted with diethyl ether. The ether layer was dried and the product was isolated by fractional distillation to yield 9 g of product (boiling point 190° C./1000 mbar; purity: 75%; colorless).

Workup

  1. temperaturerefluxed for 39.5 hours
  2. filtrationThe solid was filtered off
  3. washwashed with petroleum ether and acetone
  4. additionTo the liquid layer, 2.0 g of 1,8-diazabicyclo-[5.4.0]-undec-7-ene was added
  5. temperaturethe mixture was refluxed for two days
  6. additionAfter addition of an additional 11.6 g of 1,8-diazabicyclo-[5.4.0]-undec-7-ene
  7. temperaturerefluxing for seven hours
  8. addition25 g of ethyl acrylate was added
  9. distillationthe solvent was distilled off
  10. temperaturethe mixture was refluxed for 8 hours
  11. additionby adding acetic acid
  12. washwashed with an aqueous potassium carbonate solution
  13. extractionextracted with diethyl ether
  14. dry with materialThe ether layer was dried
  15. customthe product was isolated by fractional distillation

Sources & evidence

ORD record
ord-fb60a19a9b724238bac897d786ad9d47
Source dataset
uspto-grants-2007_01
Patent number
US07166648B2

Reaction notes

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