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

HRID 627111Notes

Reaction equation

HRID 627111 reaction equation
[OH:1][C:2]1[C:3](=[O:10])[CH:4]=[C:5]([CH2:8][OH:9])[O:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1>CN(C=O)C>[OH:9][CH2:8][C:5]1[O:6][CH:7]=[C:2]([O:1][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:3](=[O:10])[CH:4]=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]-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one (Alfa Aesar, 5.11 g, 35.96 mmol) in DMF (70 mL) at room temperature was added potassium carbonate (9.94 g, 71.92 mmol) and 1-(chloromethyl)-4-methoxybenzene (5.86 mL, 43.15 mmol) dropwise. The reaction mixture was heated at 80° C. for 1 hour then concentrated. To the resulting slurry was added ice water. The precipitate was collected by filtration then triturated with ethyl acetate and filtered again. The title compound was obtained as a tan solid (6.44 g, 68%).

Workup

  1. concentrationthen concentrated
  2. additionTo the resulting slurry was added ice water
  3. filtrationThe precipitate was collected by filtration
  4. customthen triturated with ethyl acetate
  5. filtrationfiltered again

Sources & evidence

ORD record
ord-9205ef105bfa4b0996eb1e405bc42179
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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