Butyl iodide → HCID 22678123, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyl iodide (13.2 ml, 117 mmol) was added to a mixture of methyl 5-acetylsalicylate (15 g, 77 mmol) and potassium carbonate (16 g, 117 mmol) in acetonitrile (500 ml), and the reaction stirred at 60° C. for 18 hours. TLC analysis showed starting material remaining, so additional n-butyl iodide (26.4 ml, 234 mmol) and potassium carbonate (16 g, 117 mmol) were added and the reaction stirred at 60° C. for a further 72 hours. The cooled mixture was concentrated under reduced pressure and the residue partitioned between ethyl acetate and water. The phases were separated, the organic layer washed with brine, dried (MgSO4) and evaporated under reduced pressure to afford the title compound as a yellow oil that crystallised on drying in vacuo, 17.4 g.

Provenance & Evidence