Methanol → Methyl (3R)-3-hydroxyoctanoate

HRID 610784Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 610784
[O:1]=[C:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:3][C:4]([O:6][CH3:7])=[O:5].CO.[H][H]>C(Cl)Cl.[Ru]>[OH:1][C@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 89668Methyl 3-oxooctanoateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 12550001Methyl (3R)-3-hydroxyoctanoateAusbeute 94,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23950RutheniumKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Into a 100-ml autoclave (made of Hastelloy) were introduced 20 g of methyl 3-oxooctanoate (manufactured by Inoue Perfumery Mfg. Co., Ltd., Japan) and 40 ml of methanol. The atmosphere in the autoclave was replaced with nitrogen gas. Thereto was added a solution prepared by dissolving 150 mg of Ru2Cl4 ((+)-(T)BINAP)2Et3N as a ruthenium-optically active phosphine complex in 1.2 ml of methylene chloride. Asymmetric hydrogenation was conducted at a reaction temperature of 65° C. and a hydrogen pressure of 30 atm. After the reaction mixture was thus reacted for 6 hours, it was taken out of the autoclave. The methanol was distilled off, and the residue was subjected to vacuum distillation to obtain 19.2 g of methyl (R)-3-hydroxyoctanoate. Yield, 95%.

Aufarbeitung

  1. additionThereto was added a solution
  2. customprepared
  3. customwas conducted at a reaction temperature of 65° C.
  4. customAfter the reaction mixture was thus reacted for 6 hours
  5. distillationThe methanol was distilled off
  6. distillationthe residue was subjected to vacuum distillation

Quellen und Nachweise

ORD-Eintrag
ord-b2e67f5beaa14cc2bd688aa78a597b6a
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998668

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