Quinones and quinone methides. IX. Oxidation of 2,4-Bis(1,1-dimethylethyl)-6-(4-methoxyphenylmethyl)phenol in alcoholic solvents: Monomeric products and the crystal structure of an unusual dimes, 2-[3,5-Bis(1,1-dimethylethyl)-2-{methoxy-(4-methoxyphenyl)methoxy} phenoxyl-1,5-bis(1,1-dimethylethyl)-3-[methoxy-(4-methoxyphenyl)methyl]benzene

Abstract

Oxidation of the title benzylphenol (1) with silver oxide in alcoholic media forms benzylic ethers of type (5) in high yields; e.g. oxidation in methanol yields 2,4-bis(1,1-dimethylethyl)-6-[methoxy(4- methoxyphenyl)methyl]phenol(5a) together with an unusual dimer, the structure of which was shown by X-ray crystallographic analysis to be 2-[3,5-bis(1,1-dimethylethyl)-2-{methoxy(4-methoxyphenyl)- methoxy}phenoxy]-1,5-bis(1,1-dimethylethy)-3-[methoxy(4- methoxyphenyl)methyl]benzene (6). The benzylic ethers (5) are convenient intermediates for the syntheses of a variety of compounds related to (1).