Kojic Acid → 5-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one

Participants

Reaction Steps

To a stirred solution of kojic acid (71.05 g, 0.5 mmol) and sodium hydroxide (22 g, 0.55 mol) in 750 mL of MeOH and 75 mL of water was added benzylchloride (73 g, 0.575 mmol) drop-wise. The resulting mixture was heated at reflux for 4.5 h with stirring. The mixture was then allowed to cool and concentrated to half of the starting volume. The mixture was poured into water, the resultant solid was collected, washed with water, and dried to give 110 g crude compound. The crude compound was re-crystallized from EtOAc to give 5-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one. 1H NMR 6 (400 MHz, d6-DMSO): 8.14 (s, 1H), 7.40-7.30 (m, 5H), 6.29(s, 1H), 5.68 (t, J=6.0 Hz, 1H), 4.91 (s, 2H), 4.26 (d, J=6.0 Hz,1H).

Provenance & Evidence