Hydrochloric Acid → Ethyl alpha-benzylacetoacetate

HRID 325127

Reaktionsgleichung

Reaktionsgleichung von HRID 325127
[H-].[Na+].[C:3]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:4][C:5]([CH3:7])=[O:6].[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>C1(C)C=CC=CC=1.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[CH2:10]([O:9][C:3](=[O:8])[CH:4]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:5](=[O:6])[CH3:7])[CH3:11]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 8868Ethyl AcetoacetateHCID 24758Sodium hydride

Produkt 1

HCID 246929Ethyl alpha-benzylacetoacetateAusbeute 58,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 21218Trioctylmethylammonium chlorideKatalysatorHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

To a suspension of 36.08 g 60% sodium hydride in 1000 ml of toluene, 112.9 g ethyl acetoacetate was dropped in. The temperature rose to 60° C. and then the reaction mixture was stirred for 1 hour at room temperature. Then 17.54 g Aliquat 336 were added and the reaction mixture was heated to 84° C. Now a solution of 54.90 g benzyl chloride in 50 ml of toluene was dropped in. Then the mixture was stirred at 84° C. for 26 hours. After the mixture was cooled down to room temperature, it was acidified with 250 ml of 2N HCl and extracted with ether. The combined organic phase was washed with 5% sodium bicarbonate and brine, dried, filtered and evaporated to dryness. The resulting brown oil was purified by chromatography to yield 55.74 g of a colourless oil.

Aufarbeitung

  1. additionwas dropped in
  2. customrose to 60° C.
  3. temperaturethe reaction mixture was heated to 84° C
  4. stirringThen the mixture was stirred at 84° C. for 26 hours
  5. temperatureAfter the mixture was cooled down to room temperature
  6. extractionextracted with ether
  7. washThe combined organic phase was washed with 5% sodium bicarbonate and brine
  8. customdried
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customThe resulting brown oil was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6f4f55195b8649adb12c8176c1961511
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06222062B1

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