Kojic Acid → 5-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one

HRID 234149

Reaction equation

HRID 234149 reaction equation
[CH:1]1[C:6](=[O:7])[C:5]([OH:8])=[CH:4][O:3][C:2]=1[CH2:9][OH:10].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[CH2:17]([O:8][C:5]1[C:6](=[O:7])[CH:1]=[C:2]([CH2:9][OH:10])[O:3][CH:4]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 3840Kojic AcidHCID 7503Benzyl ChlorideHCID 11430Potassium Carbonate

Product 1

HCID 9015985-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-oneYield 75.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of kojic acid (28 g) in DMF (200 ml) was added potassium carbonate (32 g), and the mixture was stirred at room temperature for 30 minutes. After benzyl chloride (25 g) was added, the mixture was further stirred for 60 minutes. The solvent was evaporated. The residue was then extracted with ethyl acetate, washed with water and dried. After the solvent was evaporated, the residue was crystallized from ethyl acetate to give 5-benzyloxy-2-hydroxymethyl-4-oxo-4H-pyran (34.6 g).

Workup

  1. stirringthe mixture was further stirred for 60 minutes
  2. customThe solvent was evaporated
  3. extractionThe residue was then extracted with ethyl acetate
  4. washwashed with water
  5. customdried
  6. customAfter the solvent was evaporated
  7. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-e50df54098a84e479a9dd6dc06e6abaf
Source dataset
uspto-grants-1997_01
Patent number
US05594004

Linked notes

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