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

Participants

Reaction Steps

To a solution of 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one (13.35 g, 94 mmol) in N,N-dimethylformamide (160 ml) stirred under nitrogen at 0° C. was added a solution of potassium tert-butoxide (12.65 g, 113 mmol) in N,N-dimethylformamide (40.0 ml) dropwise over 10 min. The mixture was then stirred at room temperature for 90 minute and 4-methoxybenzyl chloride (15.5 ml, 114 mmol) was added dropwise over 15 min and allowed to stir at 50° C. for 3 days. The reaction was cooled and concentrated under vacuum. Water (400 mL) was added, the resulting precipitate was filtered, washed with water, collected and dried to afford 2-(hydroxymethyl)-5-((4-methoxybenzyl)oxy)-4H-pyran-4-one (18.17 g, 69.3 mmol, 73.8% yield) as tan solid. LCMS: (M+H)+: 263.0

Provenance & Evidence