Iodoethane → Methyl 4-ethoxy-2-hydroxybenzoate

Participants

Reaction Steps

Methyl 4-hydroxysalicylate (10.0 g, 59.5 mmol) was dissolved in DMF. Ethyl iodide (9.74 g, 62.4 mmol) was added, followed by potassium carbonate (8.63 g, 62.4 mmol), and the reaction mixture was stirred under N2 at room temperature for 18 h. The reaction mixture was concentrated in vacuo to remove the majority of the DMF, and the residue taken up in EtOAc, and washed with water (2×), dried, and concentrated in vacuo to give an off-white solid. Recrystallization from hexane gave 6.41 g, (54.9%) of methyl 4-ethoxysalicylate as an off-white solid.

Provenance & Evidence