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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence