Abstract The title compound, Φ2CHOH [Φ = 2,6-(MeO)2C6H3] (1), reacted in acetone under mild conditions in the presence of acid to give a new ketone, Φ2CHCH2COMe. Analogous reactions were observed in some other alkyl ketones and aldehydes, such as diethyl ketone, methyl phenyl ketone, 2,4-pentanedione, propanal, and butanal. In ethyl methyl ketone, an 80 : 20 mixture of Φ2CHCHMeCOMe and Φ2CHCH2COEt was obtained in agreement with the pKE values of two enols derived from ethyl methyl ketone. Compound 1 reacted in primary and secondary alcohols to give the reduced compound, Φ2CH2 (6), and the corresponding aldehyde and ketone derived from the alcohols, respectively. The reactivity of the alcohols was in the order, 1-propanol ≈ 1-butanol < ethanol < 2-butanol < 2-propanol. Compound 1 also reacted in ethers, such as tetrahydrofuran and diethyl ether, to give 6. It was either recovered unreacted from 2-methyl-2-propanol and from dimethyl sulfoxide, or it reacted under more forcing conditions to give products derived by Φ–C bond cleavage, followed by reactions of 1 with ΦH.