New methods for the synthesis of symmetric 5,5'-disubstituted bis-and 5,5',5"-trisubstituted tris(2-furyl)methanes have been developed. Symmetric bis(2-furyl)methanes were prepared from 5-substituted 2-furylmethanols in the presence of concentrated perchloric acid. The attempted synthesis of (aryl)[bis(2-furyl)]methanes from (aryl)(2-furyl)methanols in the presence of acid catalysts failed. The reaction of 5-substituted 2-furaldehydes with ethylene glycol in the presence of strong acid catalysts led to tris(2-furyl)methanes. Plausible mechanisms of these transformations are discussed.