4-Coumaric acid → HCID 3126208, compound

Participants

Reaction Steps

In 50 ml of dimethyl sulfoxide was suspended 15.5 g of 4-hydroxycinnamic acid, 30.0 g of bromoheptyl and 50.0 g of potassium carbonate, and were vigorously stirred for 10 hours with a mechanical stirrer while the flask was heated in oil bath under reflux. After the obtained reaction mixture was cooled, it was filtered through Celite, and the resultant residue was washed with 300 of ethyl acetate. After 500 ml of water was added to the washed mixture and the mixture was extracted with 2.5 liter of ethyl acetate, the obtained extract (organic layer) was concentrated by removing the solvent in vacuo. To the resultant residue was added 100 ml of ethanol, an aqueous solution (20 ml) containing sodium hydroxide of 10 g was added and stirred at 80° C. for 1 hour. After the resultant reaction mixture was cooled, the precipitated crystals were filtered in vacuo, and the residue was washed with 100 ml of ethanol. The washed residue was placed in 300 of dilute hydrochloric acid of 40° C., and stirred for 1 hour. The reaction mixture was filtered in vacuo and dried to obtain the above compound (e) of 19.1 g (yield: 78%).

Provenance & Evidence