2-Acetylhydroquinone → 1-(2-Hydroxy-5-propoxyphenyl)ethan-1-one

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Reaction Steps

10 g of 2,5-dihydroxyacetophenone suspended in 100 ml of acetone are placed in a 500 ml round-bottomed flask and 9.14 g of anhydrous K2CO3 are added, followed by addition of 12.4 g of propyl iodide. The reaction medium is refluxed for 30 hours. After cooling to room temperature, the medium is filtered through Celite® and then concentrated. The brown oil obtained is taken up in EtOAc, filtered, washed with water, with 2M HCl solution and then with saturated NaCl solution. The organic phase is evaporated to give a black paste. The paste is taken up in chloroform and filtered. The medium is concentrated to give 11.4 g of a black solid. This solid is taken up in absolute ethanol. The solution is placed in a freezer for 10 minutes; a solid precipitates out, and is collected by filtration. The filtrate is concentrated, taken up in ethanol, cooled in a freezer and then filtered again. This operation is repeated four more times to give 8.35 g of the expected compound in the form of a powder.

Provenance & Evidence