Diethyl Ether → Azobenzene

Participants

Reaction Steps

A flask was charged with 1.008 g of the 11-[4-(phenylazo)phenyloxy]undecanamide, 0.624 g of aluminum lithium hydride, and 40 mL of dry diethylether, and the contents were put under reflux for 12 hours. The temperature was set back to a room temperature, and 20 mL of water was gradually dropped, so as to cause the excess aluminum lithium hydride to react with the water. Thereafter, the reaction solution was stirred for one day. Then, extraction from the reaction solution was performed three times by using 200 mL of diethylether, and the diethylether was removed by pressure-reduction. After that, a remaining supernatant was purified by recrystallization from a mixed solvent of chloroform and hexane. As a result, an intended amine derivative of 4-(phenylazo)benzene including a spacer group, i.e. 4-(11-aminoundecyloxy)azobenzene (azobenzene-O—(CH2)11NH2) was obtained at a 76% yield. A structure of the 4-(11-aminoundecyloxy)azobenzene was confirmed from a 1H-NMR spectrum and a 13C-NMR spectrum.

Provenance & Evidence