Ethyl Acetoacetate → 4-(2-Ethoxycarbonyl-3-oxobutyl)biphenyl

HRID 1599360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1599360
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[Na].Cl[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1>C(O)C>[CH2:8]([O:7][C:1]([CH:2]([C:3](=[O:4])[CH3:5])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:15][CH:14]=1)=[O:6])[CH3:9]

Komponenten

5

Edukt 3

HCID 8868Ethyl AcetoacetateHCID 154634-Phenylbenzyl chlorideHCID 5360545Sodium

Produkt 1

HCID 133237014-(2-Ethoxycarbonyl-3-oxobutyl)biphenylAusbeute 95,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel3×

Versuchsvorschrift

In a four-necked flask equipped with a thermometer, dropping funnel and stirrer were placed 179 g (1.375 moles) of ethyl acetoacetate and 500 ml of ethanol, and then 31.5 g (1.375 moles) of sodium was added in portions thereto to form a solution. Then, a solution of 253.5 g (1.25 moles) of 4-chloromethylbiphenyl in 1000 ml of ethanol was added dropwise to the above solution at room temperature over a period of 2 hours. After completion of the addition, the resulting mixture was brought up to 65° C. and stirred at the temperature for 6 hours. After completion of the reaction ethanol was distilled off under reduced pressure, the residue obtained was extracted by addition of 1500 ml of toluene, and the organic layer was separated. The organic layer was washed with 10% hydrochloric acid, water, 5% aqueous sodium bicarbonate solution and water in said order and then concentrated under reduced pressure to obtain 353.5 g of 4-(2-ethoxycarbonyl-3-oxobutyl)biphenyl as a crude product.

Aufarbeitung

  1. customIn a four-necked flask equipped with a thermometer
  2. customto form a solution
  3. additionAfter completion of the addition
  4. customwas brought up to 65° C.
  5. distillationwas distilled off under reduced pressure
  6. customthe residue obtained
  7. extractionwas extracted by addition of 1500 ml of toluene
  8. customthe organic layer was separated
  9. washThe organic layer was washed with 10% hydrochloric acid, water, 5% aqueous sodium bicarbonate solution and water in said order
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b21472884f8c45c083b37dd039c8d804
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05741438

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