Hydrochloric Acid → 4-Pentenoic acid, 5-(2-methylphenyl)-3-oxo-, eth

Participants

Reaction Steps

To a solution of 2-methylcinnamic acid (50.71 g, 312.7 mmol) in tetrahydrofuran (500 ml) was added 1,1′-carbonyldiimidazole (55.8 g, 344 mmol) at room temperature, and the mixture was stirred as it was for 1 hr. To the mixture were added monoethyl malonate monopotassium salt (58.5 g, 344 mmol) and magnesium chloride (16.4 g, 172 mmol) at room temperature, and the mixture was stirred at 60° C. overnight. The reaction solution was diluted with ethyl acetate and water and acidified with conc. hydrochloric acid. The ethyl acetate layer was separated, and the aqueous layer was extracted with ethyl acetate. The recovered organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-6/1) to give the objective substance.

Provenance & Evidence