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 12.4 g of propyl iodide. The reaction medium is refluxed for 30 hours. After a return to ambient temperature, the medium is filtered through Celite® and then concentrated. The brown oil obtained is taken up in EtOAc, filtered, and washed with water, with a 2M HCl solution and then with a saturated NaCl solution. The organic phase is evaporated off 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. The latter is taken up in absolute ethanol. The solution is placed in a freezer for 10 minutes, and a solid precipitates 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 4 times to give 8.35 g of the expected compound in the form of a powder.

Provenance & Evidence