REACTIONS OF BIS(2,6-DIMETHOXYPHENYL)METHANOL IN COMMON ORGANIC-SOLVENTS IN THE PRESENCE OF AN ACID

The title compound, Phi(2)CHOH [Phi = 2,6-(MeO)(2)C6H3] (1), reacted i n acetone under mild conditions in the presence of acid to give a new ketone, Phi(2)CHCH(2)COMe. Analogous reactions were observed in some o ther alkyl ketones and aldehydes, such as diethyl ketone, methyl pheny l ketone, 2,4-pentanedione, propanal, and butanal. In ethyl methyl ket one, an 80:20 mixture of Phi(2)CHCHMeCOMe and Phi(2)CHCH(2)COEt was ob tained in agreement with the pK(E) values of two enols derived from et hyl methyl ketone. Compound 1 reacted in primary and secondary alcohol s to give the reduced compound, Phi(2)CH(2) (6), and the corresponding aldehyde and ketone derived from the alcohols, respectively. The reac tivity of the alcohols was in the order, 1-propanol approximate to 1-b utanol < ethanol < 2-butanol < 2-propanol. Compound 1 also reacted in ethers, such as tetrahydrofuran and diethyl ether, to give 6. It was e ither recovered unreacted from 2-methyl-2-propanol and from dimethyl s ulfoxide, or it reacted under more forcing conditions to give products derived by Phi-C bond cleavage, followed by reactions of 1 with Phi H .