We synthesized polymers that overcome the processing problems associated with aromatic polyanhydrides. In this paper, we focus on the synthesis and characterization of ortho-substituted polyanhydrides, poly[1,3-bis(o-carboxyphenoxy)propane anhydride] (o-CPP) and poly[1,6-bis(o-carboxyphenoxy) hexane anhydride] (p-CPH). By lengthening the alkyl chain between aryl groups (from propane to hexane) and changing the ring substitution pattern from para- to ortho-, we observed enhanced solubility of aromatic polyanhydrides. Ultimately, these polyanhydrides may be useful as polymer scaffolds for use as functional soft tissue substitutes.