Hydrochloric Acid → HCID 19778560, compound

Participants

Reaction Steps

A mixture of 20 g (0.03 mole) 12,14-Diphenyl-12,14-bis(trifluoromethyl) -12H,14H-5,7-dioxapentacene-2,3,9,10-tetracarboxylic acid, 25 g copper powder and 100 ml quinoline was refluxed vigorously for 4 hours. The cooled mixture was poured into a cold solution of 30 ml concentrated HCl in 300 ml water. The product was extracted with methylene chloride, and the extracts were passed through a column of alumina, and the eluate was stripped. The residue was stirred with methanol, and was filtered yielding 2.5 g (16 %) of a solid in two crops. The crude material melted at 203-213° C., in line with the presence of cis- and trans- isomers. The title compound was purified by vacuum sublimation at 0.6 Torr and 200° C., and melted then at 209-215° C. Analysis: Calc. for C34H20F6O2 : C 71.1; H 3.48, F 19.9; found: C 71.4; H 3.65; F 19.9 %. The mass spectrum showed presence of two isomers in about 2:1 ratio, and a parent peak at 574, with peaks at 505 and 436 m/e showing loss of one and two CF3 groups, respectively. The NMR spectrum had complex multiplets in the 7.2-7.35 and 6.9-7.1 ppm range (totaling 17 Hs), plus two pairs of broad singlets at 6.86+6.84 ppm (2H) and 6.32+6.22 ppm (1H). The coefficient of thermal expansion (CTE) was found to be 34 ppm (0-200° C.) by thermomechanical analysis (TMA) at 10° C. per minute.

Provenance & Evidence