Tributylamine → 1,20-Eicosanediol

Participants

Reaction Steps

Hydrogenation of 10-eicosene-1,20-diol: Two hundred fifty grams of the 10-eicosene-1,20-diol were placed in a twelve liter flask outfitted with a heating mantle, mechanical stirrer, condenser, and nitrogen inlet. Three liters of xylenes were added. Two equivalents each tributylamine and toluenesulfonhydrazide were added. Stirring and nitrogen flow were initiated and the solution slowly heated until the reaction was at reflux. The reaction was refluxed overnight, and then cooled to room temperature. The product, 1,20-eicosanediol, precipitated from solution and was filtered, washing with methanol. The crude product was recrystallized once from methanol, yielding white crystals with a melting point of about 101° C. The product was 99% pure by gas chromatography. IR(KBr): 3419, 3357, 2919, 2848, 1469, 1355, 1321, 1124, 1055, 1034, 999, 969, 722, 610, 502 cm−1; 1H NMR(300 MHz, toluene-d8, elevated temperature): * 3.3 (t, 4H), 1.3 (bd, 36H), 0.5 (m, 2H).

Provenance & Evidence