Methyl morpholine oxide → Hydrobenzoin

HRID 1935293Notes

Reaction equation

HRID 1935293 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N+]1([O-])CC[O:19]CC1.[OH2:23].CC(C)=O.C(#N)C>>[C:1]1([CH:7]([OH:19])[CH:8]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[OH:23])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 82029Methyl morpholine oxideHCID 638088trans-Stilbene2×HCID 18799168Acetonitrile acetone water

Product 1

HCID 95447HydrobenzoinYield 93%

Procedure

Catalytic dihydroxylation reaction of trans-stilbene by using LDH-osmate of the formula IIa LDH-osmate of the formula IIa (0.02 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 the reaction LDH-osmate catalyst was filtered off and washed with methanol. 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%). The experimental results in the Examples 9 to 24 were tabulated in Table 1&2.

Workup

  1. filtrationwas filtered off
  2. washwashed with methanol
  3. concentrationThe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-378ddd4b47ea40068a4953b882afc09e
Source dataset
uspto-grants-2002_05
Patent number
US06387033B1

Reaction notes

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