Triarylmethanols of type (4-YC6H4)Φ2COH {Φ = 2,6-(MeO)2C6H3; Y = MeO, Cl, Me2N} were prepared. The methanol, (4-MeOC6H4)Φ2COH, reacted with acids in a variety of solvents to give the triarylcarbenium salts, [(4-MeOC6H4)Φ2C]X or [(4-HOC6H4)Φ2C]X, or 4-bis(2,6-dimethoxyphenyl)methylene-2,5-cyclohexadienone, O=C6H4=CΦ2, depending on the conditions. These carbenium salts further reacted in alcohols, ROH, to give the triarylmethanes, (4-ROC6H4)Φ2CH (R = Me, Et), where the para-substituent, MeO or HO, was substituted by the solvent, accompanied by a reduction at the central carbon. The methanol, (4-ClC6H4)Φ2COH, also reacted with acid to give the carbenium salt or the triarylmethane, depending on the conditions. While the methanol, (4-Me2NC6H4)Φ2COH, also gave the carbenium salt, [(4-Me2NC6H4)Φ2C]X, it was inert against the formation of the triarylmethane under analogous conditions. It reacted with aqueous sodium hydroxide to give O=C6H4=CΦ2 rather than the original methanol. The para-substituent of [(4-MeOC6H4)Φ2C]X was substituted by di- and monoalkylamines, RR′NH, to give [(4-RR′ NC6H4)Φ2C]X (R,R′ = Me,Me; Et,Et; Me,H; Et,H; Bu,H). While [(4-ClC6H4)Φ2C]X reacted with the dialkylamines to give [(4-RR′NC6H4)Φ2C]X, it reacted with monoalkylamines, RNH2, to give [(4-ClC6H4)Φ2C–NRH2]X. [(4-Me2NC6H4)Φ2C]X was hydrolyzed in the presence of diethylamine to give O=C6H4=CΦ2, but reacted with monoalkylamines to give RN=C6H4=CΦ2.