Hydrochloric Acid → 3-Hydroxy-2,6-bis(hydroxymethyl)-4-pyrone

Participants

Reaction Steps

In a 100 mL round bottom flask were added Kojic acid (FLUKA, 5 g), 1N NaOH (39 mL) and H2O (10 mL). The mixture was cooled (ice/water bath) and 37% aqueous formaldehyde (ALDRICH, 2.9 mL) was added dropwise. After 34 h at room temperature aditional 37% aqueous formaldehyde (ALDRICH, 0.5 mL) was added dropwise and the solution allowed to stir for 18 h. The mixture was acidified by adding concentrated HCl, and the solvent eliminated to dryness under vacuum to give a crude product which was treated with chilled water to afford a solid precipitated which was filtered and vacuum dried. 3.056 g of the title compound were obtained as a white solid. The filtrate was concentrated under vacuum and a second crop of solid separated. An additional 1.154 g of the title compound were obtained.

Provenance & Evidence