Potassium Iodide → Methyl 4-(benzyloxy)-2-hydroxybenzoate

Participants

Reaction Steps

Methyl 4-hydroxysalicylate (20.0 g, 119 mmol) was dissolved in DMF (400 ml), then potassium carbonate (17.2 g, 125 mmol) and benzyl bromide (21.4 g, 125 mmol) were added, using additional DMF (400 ml) to aid the transfer. Potassium iodide (3.0 g) was added, and the reaction mixture was stirred at room temperature under nitrogen for 48 h. The DMF was removed in vacuo, the residue taken up in EtOAc, washed with water (3×), brine, and dried. The organic layer was concentrated in vacuo, and the crude product recrystallized from EtOAc:hexane to give 17.9 g (61.1%) of a white solid. A second recrystallization of material recovered from the filtrate yielded an additional 6.2 g (21.2%) of product.

Provenance & Evidence