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

HRID 1885266Notes

Reaction equation

HRID 1885266 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]Br)=[CH:21][CH:20]=1>CN(C)C=O.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

6

Reactant 3

HCID 3840Kojic AcidHCID 11430Potassium CarbonateHCID 1650214-Methoxybenzyl bromide

Product 1

HCID 104916984H-Pyran-4-one, 2-(hydroxymethyl)-5-[(4-methoxyphenyl)methoxy]-Yield 88.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of kojic acid (50 g: 0.32 Mol.) in dimethylformamide (300 ml) are added potassium carbonate (63 g: 1.42 Eq.) and p-methoxybenzyl bromide (92 g: 1.42 Eq.), and the mixture is stirred at room temperature for 2 hours. The reaction mixture is diluted with water (1liter) to give 5-p-methoxybenzyloxy-2-hydroxymethyl-4-pyrone (74.5 g). Yield: 81%. mp. 124°~130° C.

Sources & evidence

ORD record
ord-7e73fe67368c4920b1b43b37e919edbb
Source dataset
uspto-grants-1992_09
Patent number
US05143910

Reaction notes

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