Kojic Acid → 4H-Pyran-4-one, 2-(hydroxymethyl)-5-[(4-methoxyphenyl)methoxy]-

HRID 1073737Notes

Reaction equation

HRID 1073737 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+].[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1>CN(C)C=O>[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][O:8][C:5]2[C:6](=[O:7])[CH:1]=[C:2]([CH2:9][OH:10])[O:3][CH:4]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 3840Kojic AcidHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 104916984H-Pyran-4-one, 2-(hydroxymethyl)-5-[(4-methoxyphenyl)methoxy]-Yield 76.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 42.6 g kojic acid in 350ml N,N-dimethylformamide, were added 82.8 g anhydrous potassium carbonate and 55 g p-methoxybenzyl chloride, and the mixture was heated at 70°-75° C. for 1.5 hours. The reaction mixture was concentrated to about half its volume, and the concentrate was added to 700 ml water under ice cooling. The precipitate which separated out was collected by filtration, washed with water and ethyl acetate in that order, and dried, giving 59.9 g of 5-p-methoxybenzyloxy-2-hydroxymethyl-4-pyrone.

Workup

  1. temperaturethe mixture was heated at 70°-75° C. for 1.5 hours
  2. concentrationThe reaction mixture was concentrated to about half its volume
  3. additionthe concentrate was added to 700 ml water under ice cooling
  4. customThe precipitate which separated out
  5. filtrationwas collected by filtration
  6. washwashed with water and ethyl acetate in that order
  7. customdried

Sources & evidence

ORD record
ord-fbee263665f1489ca7ce36a2c3c70bbb
Source dataset
uspto-grants-1990_11
Patent number
US04971961

Reaction notes

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