A series of diyne substituted 2-hydroxy acids and derivatives have been prepared and characterized. Alkylation of butane-2,3-diacetal protected glycolic acid with haloalkyl substituted diyne compounds gave the corresponding diacetal protected diyne substituted 2-hydroxy acids. Diacetal deprotection through acid mediated hydrolysis, transesterification, or aminolysis afforded the 2-hydroxy-diyne acid, ester, or amide derivatives, respectively. A novel class of polydiacetylenes was produced through topochemical polymerization of a 2-hydroxy diyne acid and compared with the polymerization of non-hydroxylated diyne acids.