Potassium Iodide → HCID 10780025, compound

Participants

Reaction Steps

A solution of methyl 2,4-dihydroxybenzoate (6.73 g) in acetone (250 mL) is treated with potassium iodide (2.66 g), tetrabutylammonium chloride (0.05 g), potassium carbonate (5.53 g), and 4-chlorobenzyl chloride (7.08 g), and stirred at reflux for 24 hours. The mixture is filtered, and the filtrate evaporated. The residue is taken up in ethyl acetate, washed with water, dried, and evaporated. The residue is recrystallized from ethyl acetate to yield methyl 2-hydroxy-4-(4-chlorobenzyloxy)benzoate as colourless crystals (5.3 g, 45%), m.p. 119-121° C. 1H NMR (DMSO) 3.9(3H,s), 5.2(2H,s), 6.6(2H,m), 7.5(4H,m), 7.7(1H,d).

Provenance & Evidence