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

HRID 627290Notes

Reaction equation

HRID 627290 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=O)C>[OH:10][CH2:9][C:2]1[O:3][CH:4]=[C:5]([O:8][CH2:23][C:22]2[CH:25]=[CH:26][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)[C:6](=[O:7])[CH:1]=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 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred slurry of kojic acid (500 g, 3.518 mol) in dry DMF (5 L) was added dry potassium carbonate (972 g, 7.036 mol) followed by 4-methoxy benzyl chloride (661 g, 4.221 mol) at 0° C. The reaction mixture was warmed to room temperature and then heated at 80° C. for 3 hours. After cooling to room temperature the reaction mixture was poured into ice cold water (15 L) and stirred vigorously. The precipitate was collected by filtration and dried under vacuum to afford the title compound as a pale brown solid (687 g, 75%).

Workup

  1. temperatureheated at 80° C. for 3 hours
  2. temperatureAfter cooling to room temperature the reaction mixture
  3. filtrationThe precipitate was collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-6de0d862a66c47c98d78328a88117be9
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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