Acetone → Methyl 2-(2-methoxy-2-oxoethoxy)benzoate

Participants

Reaction Steps

To a mixture of methyl salicylate (100 grams, 657 mmol), anhydrous K2CO3 (360 grams, 2.605 mol) in anhydrous acetone (1000 mL) was added methyl chloro acetate (94 grams, 866 mmol) and refluxed for 36 hours. Acetone was distilled and water (1200 mL) was added. Crude 5 was extracted into Chloroform, dried over Na2SO4 distilled and purified by column chromatography on silica gel using Hexane as eluant to give pure 5 (25 grams, 17%) as a light yellow syrup. The structure was confirmed by NMR. IHNMR (CDCl3) δ 3.79 (s, 3H, ester), 3.88 (s, 3H, ester), 4.70 (s, 2H, OCH2), 6.88 (dd, 1H, Ar), 7.03 (m, 1H, Ar), 7.42 (m, 1H, Ar), 7.81 (dd, 1H, Ar).

Provenance & Evidence