Benzaldehyde → 1-Hydroxy-2-methyl-1-phenyl-3-pentanone

HRID 22060

Reaktionsgleichung

Reaktionsgleichung von HRID 22060
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([C:11]([CH2:13][CH3:14])=[O:12])[CH3:10]>>[C:2]1([CH:1]([OH:8])[CH:9]([CH3:10])[C:11](=[O:12])[CH2:13][CH3:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 240BenzaldehydeHCID 7288Ethyl ketone

Produkt 1

HCID 5460171-Hydroxy-2-methyl-1-phenyl-3-pentanoneAusbeute 72 %

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

50 mmol (5.1 ml) of benzaldehyde are added at -78° C. to the manganous enolate of diethyl ketone, prepared by the procedure described above. After stirring for 10 seconds at -78° C., the reaction medium is hydroIyzed by the dropwise addition of a saturated solution of (NH4)2SO4. After decantation, filtration on hyflo-supercel and evaporation of the solvents under vacuum, 5-phenyl-5-hydroxy-4-methylpentan-3-one is isolated by low pressure liquid chromatography on 15 μm silica gel using cyclohexane/ethyl acetate (90/10) as the eluent. Yield=72%. Erythro/threo=61/39.

Aufarbeitung

  1. customprepared by the procedure
  2. filtrationAfter decantation, filtration
  3. customon hyflo-supercel and evaporation of the solvents under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-eb2ffed42db34070991af4f46a60fd88
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05426201

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