2,2,2-Trifluoroacetophenone → 9-Phenyl-9-trifluoromethyl-2,7-dimethylxanthene

Participants

Reaction Steps

A mixture of 114 g (0.54 mole) p-tolyl ether (X), 100 g (0.54 mole) trifluoromethyl phenyl ketone, and 160 g (8 moles) HF was heated in an autoclave for 8 hrs at 130°. After venting excess HF, the reaction mixture was quenched in 2 L ice water, containing 500 ml 50% NaOH. The product was extracted with methylene chloride, the extracts were filtered through a layer of alumina, stripped and distilled in vacuo. There was obtained 140 g (73%) of distillate boiling at 186-210°/2 Torr. The solid was recrystallized from methanol or isopropyl alcohol. M.p. 150-151°. NMR: d 7.40, m 7.30, s 7.07, s(b) 6.64, s 2.16 ppm in 2:3:4:2:6 ratio. Analysis: Calc. for C22H17F3O: C 74.6; H 4.80; F 16.1; Found: C 74.7; H 4.90; F 15.9%.

Provenance & Evidence