Acta Crystallographica Section C

Crystal Structure Communications

Volume 59, Part 12 (December 2003)

Acta Cryst. (2003). C59, o700-o702 [doi:10.1107/S0108270103024673]

Bis(2,5-dimethoxy-4-methylphenyl)methane and bis(2,5-dimethoxy-3,4,6-trimethylphenyl)methane

D. J. Wiedenfeld, V. N. Nesterov, M. A. Minton and D. R. Glass

Abstract: Bis(2,5-dimethoxy-4-methylphenyl)methane, C₁₉H₂₄O₄, (IIa), was obtained and characterized as a minor product from the reaction of toluhydroquinone dimethyl ether (1,4-dimethoxy-2-methylbenzene) with N-(hydroxymethyl)trifluoroacetamide. Similarly, bis(2,5-dimethoxy-3,4,6-trimethylphenyl)methane, C₂₃H₃₂O₄, (IIb), was prepared from the corresponding reaction of trimethylhydroquinone dimethyl ether (2,5-dimethoxy-1,3,4-trimethylbenzene). The molecules of (IIa) and (IIb) each lie on a twofold axis passing through the methylene group. The dihedral angle between the planar phenyl rings is 73.4 (1)° in (IIa) and 77.9 (1)° in (IIb). The external bond angles around the bridging methylene group are 116.6 (2) and 117.3 (2)° for (IIa) and (IIb), respectively. In (IIa), the methoxy substituents lie in the plane of the ring and are conjugated with the aromatic system, whereas in (IIb), they are almost perpendicular to the phenyl ring and are positioned on opposite sides.

Formula: C₁₉H₂₄O₄ and C₂₃H₃₂O₄

Online 14 November 2003


	Structure factor file (CIF format) (91.5 kbytes) Contains datablock IIa

	Structure factor file (CIF format) (99.5 kbytes) Contains datablock IIb

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