Flotation reagents are the critical technique in the flotation separation process for desilication. Aimed at the highly selective reagent for direct flotation of diasporic bauxite, a novel compound, dibenzo-1-(7-carboxyl-4-hydroxyl bicycle [2.2.2] octan-7,8-diyl) carboxamic acid (DBCA) with two functional groups carboxyl and hydroxamate in the same molecule, was synthesized through Diels-Alder reaction followed by oximation reaction. Subsequently, the floatability of diaspore, kaolinite, and illite was measured by using DBCA as a collector, the interaction mechanism between minerals and DBCA was investigated through zeta potential measurements and FT-IR spectrum, and the structure and property relationship of the collector were also discussed. The flotation experimental results showed that DBCA had a very strong collecting ability for diaspore, while poor activity was observed for kaolinite and illite. The interaction of DBCA on diaspore surfaces may be mainly dominated by chemical bonding as the formation of three chelation rings; however, those on the surfaces of kaolinite and illite are mainly hydrogen bonding or physical adsorption. Consequently, it is possible to separate diaspore from such aluminosilicates as kaolinte and illite employing DBCA as a collector.