1-Phenylethanol → Butanoic acid, 3-oxo-, 1-phenylethyl ester

HRID 843313

Reaktionsgleichung

Reaktionsgleichung von HRID 843313
[C:1](OC)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[C:9]1([CH:15]([OH:17])[CH3:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[C:1]([O:17][CH:15]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:16])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4]

Komponenten

4

Edukt 2

HCID 74091-Phenylethanol2×HCID 7757Methyl acetoacetate2×

Produkt 1

HCID 38515Butanoic acid, 3-oxo-, 1-phenylethyl esterAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

In this example, procedure of transestrification of methyl acetoacetate with 1-phenyl ethanol is described. A mixture of 1 equivalent of methyl acetoacetate, 1 equivalent of 1-phenyl ethanol and 100 mg of sulfated tin oxide catalyst in 20 ml of toluene was heated to 110° C. in a two necked round bottom flask provided with a distillation condenser to remove methanol. The reaction was monitored by thin layer chromatography (TLC). After completion of the reaction (about 6 hours), the catalyst was filtered and the filtrate was concentrated and chromatographed on a silica gel column (95% petroleum ether and 5% ethyl acetate) to afford 1-phenylethyl acetoacetate as a viscous colorless liquid in 97% yield.

Aufarbeitung

  1. customprovided with a distillation condenser
  2. customto remove methanol
  3. customAfter completion of the reaction (about 6 hours)
  4. filtrationthe catalyst was filtered
  5. concentrationthe filtrate was concentrated
  6. customchromatographed on a silica gel column (95% petroleum ether and 5% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f66ba860662e44e1a8383ce36972bb92
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06376701B1

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