Methanol → 4-Hydroxy-1-phenyl-1-pentanone

HRID 2226690

Reaktionsgleichung

Reaktionsgleichung von HRID 2226690
[C:1]1([C:7](=[O:13])[CH2:8][CH2:9][C:10](=[O:12])[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO>C(Cl)Cl>[OH:12][CH:10]([CH3:11])[CH2:9][CH2:8][C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:13]

Komponenten

4

Edukt 2

HCID 887MethanolHCID 1363711-Phenyl-1,4-pentanedione

Produkt 1

HCID 1548894-Hydroxy-1-phenyl-1-pentanoneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A 100-ml stainless steel autoclave purged with nitrogen in advance was charged with 5 g (0.0284 mol) of 5-phenyl-2,5-pentanedione and 10 ml of methanol. A solution of 0.2 g (0.142 mmol) of [RuI(p-cymene)((R)-T-BINAP)]I3 in 2 ml of methylene chloride was added thereto, thereby conducting reaction at a reaction temperature of 50° C. for 40 hours under a hydrogen pressure of 50 kg/cm2. After distilling off the solvent, the residue was purified by column chromatography on a silica gel using a developing solvent of hexane/ethyl acetate (5/1) to obtain 4.5 g of (-)-4-hydroxy-1-phenylpentane-1-one (yield: 90.0%).

Aufarbeitung

  1. customA 100-ml stainless steel autoclave purged with nitrogen in advance
  2. customreaction at a reaction temperature of 50° C. for 40 hours under a hydrogen pressure of 50 kg/cm2
  3. distillationAfter distilling off the solvent
  4. customthe residue was purified by column chromatography on a silica gel using a developing solvent of hexane/ethyl acetate (5/1)

Quellen und Nachweise

ORD-Eintrag
ord-ed37c936785b4937af54c0a65986c3cd
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05349107

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