Kojic Acid → HCID 14749913, compound

HRID 2081668Notes

Reaction equation

HRID 2081668 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH3:4].[CH:6]1[C:11](=[O:12])[C:10]([OH:13])=[CH:9][O:8][C:7]=1[CH2:14][OH:15].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[CH2:1]([O:13][C:10]1[C:11](=[O:12])[CH:6]=[C:7]([CH2:14][OH:15])[O:8][CH:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 3840Kojic AcidHCID 4875Potassium IodideHCID 8002Butyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 14749913HCID 14749913, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

48.3 g (0.352 mole) 1-butyl bromide are added at ambient temperature, with vigorous stirring, to a mixture of 50 g (0.352 mole) kojic acid, 48.7 g (0.352 mole) potassium carbonate, 1 g potassium iodide and 420 mL anhydrous dimethylformamide. Thereafter, the reaction mixture is stirred for 3 hours at 90° C. After cooling, the solvent is removed under vacuum and the residue is mixed with water and extracted with dichloromethane. The organic phase is separated off and dried, the solvent is evaporated and the residue is recrystallized from ethyl acetate. There is obtained a solid, colorless product; m.p. 68°-73° C.

Workup

  1. temperatureAfter cooling
  2. customthe solvent is removed under vacuum
  3. additionthe residue is mixed with water
  4. extractionextracted with dichloromethane
  5. customThe organic phase is separated off
  6. customdried
  7. customthe solvent is evaporated
  8. customthe residue is recrystallized from ethyl acetate
  9. customThere is obtained a solid, colorless product

Sources & evidence

ORD record
ord-04f2d09b617542a78811ad595dba259f
Source dataset
uspto-grants-1993_02
Patent number
US05185352

Reaction notes

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