Methyl Salicylate → HCID 69098843, compound

Participants

Reaction Conditions

Reaction Steps

Methyl salicylate (4.6 g, 30 mmol) was treated with ethyl 4-bromobutyrate (6.5 g, 33 mmol) followed by the addition of potassium carbonate (4.6 g, 33 mmol), potassium iodide (61 mg, 0.36 mmol) and acetone (75 mL). The mixture was heated at reflux for 16 hours, cooled and filtered to remove the solids. The solids were washed with additional acetone and the combined filtrates were concentrated under reduced pressure. The residue was dissolved in ether (150 mL), cooled to 0° C., washed with 40 mL of 0.5 M sodium hydroxide, washed with brine, dried (MgSO4), filtered, concentrated under reduced pressure and the residue chromatographed on silica gel eluting with a gradient of hexane:EtOAc (10:1, 5:1 and 4:1) to provide the title compound. 1H NMR (CDCl3) δ 1.25 (t, J=7.12 Hz, 3H), 2.09-2.22 (m, 2H), 2.59 (t, J=7.29 Hz, 2H), 3.89 (s, 3H), 4.06-4.19 (m, 4H), 6.93-7.03 (m, J=8.14, 8.14 Hz, 2H), 7.40-7.48 (m, 1H), 7.78 (dd, J=7.63, 1.86 Hz, 1H); MS (M+H)+ m/z 267.

Provenance & Evidence