Acetonitrile → Ethyl 1,3-benzodioxole-5-propionate

Participants

Reaction Conditions

Reaction Steps

First, 50 g of 3,4-methylenedioxy cinnamic acid was dissolved in 500 ml of ethanol. To the mixture, 5 g of 5% Pd/C catalyst was added. The reaction system was replaced with hydrogen gas and stirred at 25° C. for 6 hours. After completion of the reaction, the Pd/C catalyst was removed by filtration. The resultant ethanol solution was cooled to 5° C. and 37.1 g of thionyl chloride was added dropwise for one hour. After completion of the dropwise addition, the ethanol solution was stirred for a further 3 hours with keeping the inner temperature at 5° C. After completion of the reaction, a solvent was distilled off under reduced pressure to obtain 54.7 g of an orange concentrate. A part of the concentrate was taken and analyzed by high performance column chromatography (HPLC) (column: LiChrosphere 100 PR-8(E), 250 mm×4.0 mm I.D., manufactured by Merck Ltd., mobile phase: an aqueous solution of phosphate/potassium dihydrogenphosphate: acetonitrile=1:1, flow rate: 1 ml/minute, detection wavelength: 210 nm, column temperature: 30° C.). As a result, it was observed that 49.8 g of the titled compound was obtained.

Provenance & Evidence