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

HRID 1038601Notes

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=O)C>[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

Conditions

Temperature: 50 °C

Procedure

5-Hydroxy-2-hydroxymethyl-4H-4-pyranone (5.0 g, 35.2 mmol) was dissolved in N,N′-dimethylformamide (70 mL), and potassium tert-butoxide (4.0 g, 35.2 mmol) was added under an argon atmosphere and under ice-cold conditions. 5 minutes after, 4-methoxybenzylchloride (6.06 g, 38.7 mmol) was added at the same temperature, and stirred at 50° C. for 21 hours. Then, the reaction solution was concentrated in vacuo. After adding water and an 1N aqueous solution of sodium hydroxide, the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was added diethylether for purification by recrystallization, and the title compound (4.80 g (yield 52%)) was obtained as a brown powder crystal.

Workup

concentrationThen, the reaction solution was concentrated in vacuo
additionAfter adding water
extractionan 1N aqueous solution of sodium hydroxide, the solution was extracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
additionThe obtained residue was added diethylether
customfor purification
customby recrystallization

Sources & evidence

ORD record: ord-2f147bc37ce6495d9857d42c6768afe3
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551985B2

Reaction notes

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