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

HRID 525850Notes

Reaction equation

HRID 525850 reaction equation
[OH:1][C:2]1[C:3](=[O:10])[CH:4]=[C:5]([CH2:8][OH:9])[O:6][CH:7]=1.CC(C)([O-])C.[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>[OH:9][CH2:8][C:5]1[O:6][CH:7]=[C:2]([O:1][CH2:23][C:22]2[CH:25]=[CH:26][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)[C:3](=[O:10])[CH:4]=1

Participants

5

Reactant 3

HCID 3840Kojic AcidHCID 699934-Methyloxybenzyl chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 104916984H-Pyran-4-one, 2-(hydroxymethyl)-5-[(4-methoxyphenyl)methoxy]-Yield 73.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one (13.35 g, 94 mmol) in N,N-dimethylformamide (160 ml) stirred under nitrogen at 0° C. was added a solution of potassium tert-butoxide (12.65 g, 113 mmol) in N,N-dimethylformamide (40.0 ml) dropwise over 10 min. The mixture was then stirred at room temperature for 90 minute and 4-methoxybenzyl chloride (15.5 ml, 114 mmol) was added dropwise over 15 min and allowed to stir at 50° C. for 3 days. The reaction was cooled and concentrated under vacuum. Water (400 mL) was added, the resulting precipitate was filtered, washed with water, collected and dried to afford 2-(hydroxymethyl)-5-((4-methoxybenzyl)oxy)-4H-pyran-4-one (18.17 g, 69.3 mmol, 73.8% yield) as tan solid. LCMS: (M+H)+: 263.0

Workup

  1. stirringto stir at 50° C. for 3 days
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated under vacuum
  4. additionWater (400 mL) was added
  5. filtrationthe resulting precipitate was filtered
  6. washwashed with water
  7. customcollected
  8. customdried

Sources & evidence

ORD record
ord-f2d2f95a6df84ddf9c303f80b7911749
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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