Methyl morpholine oxide → Hydrobenzoin

HRID 48542

Reaktionsgleichung

Reaktionsgleichung von HRID 48542
C[N+]1([O-])CC[O:5]CC1.[C:9]1(/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH2:23].CC(C)=O.C(#N)C>O=[Os](=O)(=O)=O>[C:9]1([CH:15]([OH:5])[CH:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[OH:23])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

5

Edukt 3

HCID 82029Methyl morpholine oxideHCID 638088trans-StilbeneHCID 18799168Acetonitrile acetone water

Produkt 1

HCID 95447HydrobenzoinAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 30318Osmium TetroxideKatalysator

Versuchsvorschrift

Resin-OsO4 (0.01 Eq. Wt.), N-methylmorpholine-N-oxide (1.5 Eq. Wt.) and trans-stilbene (1.0 Eq. Wt) in the mixed solvent of water/acetone/acetonitrile (in the volume ratio of 1:1:1) were stored at room temperature for 6 hours. After completion of the reaction, the catalyst was filtered off and washed with ethyl acetate. The combined filtrates were concentrated under reduced pressure. The pure product, 1,2-diphenyl-1,2-ethandiol was obtained by removing the solvent at reduced pressure followed by column chromatography. (yield 93%).

Aufarbeitung

  1. customAfter completion of the reaction
  2. filtrationthe catalyst was filtered off
  3. washwashed with ethyl acetate
  4. concentrationThe combined filtrates were concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-48b08089d0d9411d98ceac7e87dfb2f3
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703531B2

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