Benzene → HCID 14024762, compound

Participants

Reaction Steps

A mixture of 10.0 g (0.057 mol) trifluoroacetophenone, 100 ml of benzene, and 5 ml of trifluoromethyl sulfonic acid was stirred for 48 hours at room temperature. The product was worked up as in Example 6 to give a white crystalline mass. Thin-layer and high-pressure liquid chromatography indicated the product was a complex mixture of many components. The thin-layer chromatogram under ultraviolet light indicated the presence of many intensely white and blue fluorescent components. The product mixture was column-chromatographed on silica gel, the material then eluted with pentane, collected, and twice rechromatographed to give 6.2 g (35%), of the white crystalline triphenyl compound: m.p. 158°-159° C.; IR (KBr) 1600 and 1590 (Ar), 1150 (C-F), 760 and 695 cm-1 (monosubstituted phenyl); NMR δ 7.18 (broad singlet); mass spectrum m/e, 312 (parent ion), 243 (P-69), 165 (P-147), 120 (P-192). Analytical: calculated for C20H15F3 ; C, 76.92; H, 4.81; F, 18.2%. Found: C, 76.77; H, 4.84; F, 17.9%.

Provenance & Evidence