N,N,N',N'-Tetramethylethylenediamine → 9,9'-(Buta-1,3-diyne-1,4-diyl)dianthracene

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Reaction Steps

15 g (0.074 mol) of 9-ethynyl anthracene, 0.36 g (3.7 mmol) copper(I) chloride, 0.43 g (3.7 mmol) of N,N,N′,N′-tetramethylethylenediamine were put into a 500 ml round-bottomed flask equipped with a stirrer, and then dissolved in 200 ml of acetone. The resulting mixture was then vigorously stirred for two hours while purging oxygen gas, to give red-colored solid. After the reaction was completed, the solvent was mostly removed with a small amount remaining. The residue was then precipitated in 5% aqueous hydrochloric acid to obtain red-colored solid. The solid was filtered, washed sufficiently with water and ethanol, and then recrystallized from ethyl acetate, to give red-colored crystal. The red-colored crystal was recovered and then sufficiently dried in a vacuum oven at 40° C., to give 13 g (87.2% yield) of the desired product having a melting point of 280-282° C.

Provenance & Evidence