Methyl morpholine oxide → Hydrobenzoin

HRID 479891

Reaction equation

HRID 479891 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 95447HydrobenzoinYield 93%

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

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 stirred at room temperature for 6 hours. After completion of the reaction, the catalyst was filtered off and washed with ethyl acetate. 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%).

Workup

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

Sources & evidence

ORD record
ord-8c0ac3fdd0ad49bb8468268c9a195925
Source dataset
uspto-grants-2003_11
Patent number
US06646168B2

Linked notes

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