HCID 12896857, compound → Levoglucosenone

HRID 2248915Notes

Reaction equation

HRID 2248915 reaction equation
[C@@H:1]12[O:9][CH2:8][C@@H:6]([O:7]1)[CH2:5][CH2:4][C@H:2]2[OH:3]>ClCCl.[O-2].[O-2].[Mn+4]>[CH2:8]1[O:9][C@@H:1]2[O:7][C@H:6]1[CH:5]=[CH:4][C:2]2=[O:3]

Participants

4

Reactant 1

HCID 12896857HCID 12896857, compound

Product 1

HCID 699486LevoglucosenoneYield 83.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

[D] 19 g of 1,6-anhydro-3,4-dideoxy-β-D-galactopyranose (7) prepared in the step [C] was dissolved in 100 ml of dichloromethane, forming a solution. Then, 50 g of active manganese dioxide was added to this solution, and the solution was stirred for 2 at room temperature, thus causing a reaction. Upon completion of the reaction, manganese dioxide was filtered off, and the solvent was distilled off under reduced pressure, whereby 15.3 g of levoglucosenone (8) (i.e., 1,6-anhydro-3,4-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose) was obtained at a yield of 82%. This substance exhibited the following physical properties:

Workup

  1. customforming a solution
  2. customa reaction
  3. filtrationwas filtered off
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7fcc2136e28e40a59680be5afc5eed88
Source dataset
uspto-grants-1991_08
Patent number
US05041566

Reaction notes

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