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

HRID 2372890Notes

Reaction equation

HRID 2372890 reaction equation
[C:1]1([CH3:15])[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[C:16]1([C:22]([C:24]([F:27])([F:26])[F:25])=O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[C:16]1([C:22]2([C:24]([F:25])([F:26])[F:27])[C:5]3[CH:6]=[C:1]([CH3:15])[CH:2]=[CH:3][C:4]=3[O:7][C:8]3[C:13]2=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=3)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 99052,2,2-TrifluoroacetophenoneHCID 74098Benzene, 1,1'-oxybis[4-methyl-

Product 1

HCID 151808189-Phenyl-9-trifluoromethyl-2,7-dimethylxanthene

Procedure

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 C22 h17F3O: 74.6; H 4.80; F 16.1; Found: C 74.7; H 4.90; F 15.9%.

Workup

  1. temperaturewas heated in an autoclave for 8 hrs at 130°
  2. customthe reaction mixture was quenched in 2 L ice water
  3. additioncontaining 500 ml 50% NaOH
  4. extractionThe product was extracted with methylene chloride
  5. filtrationthe extracts were filtered through a layer of alumina
  6. distillationdistilled in vacuo
  7. customThere was obtained 140 g (73%) of distillate boiling at 186°-210/2 Torr
  8. customThe solid was recrystallized from methanol or isopropyl alcohol

Sources & evidence

ORD record
ord-fb6ce8e6c7d34f2e95b78a47e999a6a7
Source dataset
uspto-grants-1992_03
Patent number
US05101004

Reaction notes

Loading…