Methanol → 3-Benzyloxy-2-methyl-4-pyrone

Participants

Reaction Steps

20.0 g (159 mmol) of 2-methyl-3-hydroxy-4-pyranone and 22.1 g (175 mmol, 1.1 eq.) of benzyl chloride are introduced into 200 mL of methanol; then 6.98 g (175 mmol) of NaOH in 22 mL of water are added. The reaction medium is reflux agitated for 6½ hours. The solvent is subsequently evaporated and the residue retaken up with 100 mL of dichloromethane. This solution is then washed with a 5% aqueous solution of soda (2×80 mL) and with water (2×80 mL). The organic phases are collected, dried on sodium sulphate, filtered and evaporated under reduced pressure; 32.3 g (149 mmol) of 2-methyl-3-benzyloxy-4-pyranone are isolated. Yield: 94%.

Provenance & Evidence