Dimethylformamide → 2-Propynyl 4-(2-propynyloxy)-3-methoxybenzoate

Participants

Reaction Steps

To 100 ml of DMF were added 10 g of 4-hydroxy-3-methoxybenzoic acid, 15.7 g of propargyl bromide and 18 g of potassium carbonate, and the resulting mixture was stirred at room temperature for 8 hours, and then at 80° C. for 2 hours. Thereafter, ethyl acetate was added to the reaction mixture which had been allowed to cool to near room temperature, and this was filtered through Celite (registered trade mark). To the filtrate were added sequentially water and dilute hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was dried with magnesium sulfate, and concentrated under reduced pressure. The resulting crystals were washed with a mixed solvent of hexane and MTBE, and 13.2 g of 2-propynyl 4-(2-propynyloxy)-3-methoxybenzoate was obtained.

Provenance & Evidence