Acetone → HCID 68979033, compound

Participants

Reaction Steps

To a mixture of methyl ferulate (38 grams, 183 mmol), anhydrous K2CO3 (88 grams, 637 mmol), Sodium iodide (8 grams, 53 mmol), disodium phosphate (8 grams, 56 mmol) in anhydrous acetone (800 mL) was added methyl chloro acetate (27.2 grams, 251 mmol) and refluxed for 10 hours. Acetone was distilled and water (750 mL) was added. Crude 20 was filtered and recrystallized from methanol and further purified by column chromatography on silica gel using chloroform as eluant to give pure 20 (36 grams, 70.6%) as a white powder. The melting point found to be 105-106.8° C. The structure was confirmed with IR and NMR. IHNMR (CDCl3) δ 3.80 (s, 6H, ester), 3.92 (s, 3H, —OCH3), 4.64 (s, 2H, OCH2), 6.26 (d, 1H, J=17.5 Hz, CH═CH), 6.78 (d, 1H, Ar), 7.05 (m, 2H, Ar), 7.60 (d, 1H, J=17.5 Hz, CH═CH).

Provenance & Evidence