We demonstrate the unusual reactivity of Vitamin K3 with sodium ethoxide accompanying its trimerization which gave 6-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl) pentaphene-5,8,13,14-tetraone (1) as the product made up of substituted naphthoquinone and anthraquinone core. X-ray structure of the product revealed CH⋯O interaction; π-π stacking and C⋯O close contacts in its crystal. Electronic structure of 1 obtained from the M06-2X/6-311++G (d, p) theory is in consonance with the experiment. Besides the π-π stacking in its dimer are probed through the noncovalent interactions reduced density gradient analysis within the quantum theory of atoms in molecules.