Acetic Acid → 1,4-Bis(p-octyloxybenzylidene amino)anthraquinone

Participants

Reaction Steps

In a round-bottomed flask fitted with thermometer, reflux condenser and stirrer is placed a mixture of 25 ml. glacial acetic acid and 50 ml methanol and in it is dissolved 2.38 g (0.1 mol) 1,4-diaminoanthraquinone. There is taken added 4.68 g (0.2 mol) p-octyloxybenzaldehyde and the mixture is heated at 90° for one hour. The reaction mixture is cooled to about 20°-25° and poured into ice water. The precipitated product is collected and recrystallized from ethylene glycol monomethyl ether or 1:1 methanol water as small purple needles. The crystallization is repeated twice more to obtain 1,4-bis(p-octyloxybenzylidene amino)anthraquinone m.p. 280° C. (dec) having absorption spectra in visual and infra red ranges as shown in FIGS. 9, 10, and 11 and of sufficient purity for use in guest-host combinations.

Provenance & Evidence