Hydrogen Bromide → 4,4'-(2,2,2-Trifluoro-1-phenylethane-1,1-diyl)diphenol

HRID 6196

Reaction equation

HRID 6196 reaction equation
F[C:2](F)(F)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[F:13][C:14]([F:20])([F:19])S(O)(=O)=O.[C:21]1([O:27]C)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Br>C(O)(=O)C>[OH:27][C:21]1[CH:26]=[CH:25][C:2]([C:3]([C:24]2[CH:23]=[CH:22][C:21]([OH:27])=[CH:26][CH:25]=2)([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:14]([F:20])([F:19])[F:13])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 7519AnisoleHCID 99052,2,2-TrifluoroacetophenoneHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 190051754,4'-(2,2,2-Trifluoro-1-phenylethane-1,1-diyl)diphenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 100 grams (0.57 mol) of trifluoroacetophenone, 100 grams (0.7 mol) trifluoromethane sulfonic acid, and 100 grams (10.9 mol) anisole is stirred at room temperature for 24 hours. The mixture is then transferred to a separatory funnel and the organic material is washed with water (3×11), saturated bicarbonate (3×500 ml) and water (2×500 ml). The organic phase is dried and the volatiles removed in vacuo. The resulting material is crystallized from aqueous methanol. 37.2 grams (0.1 mol) of this product is refluxed with glacial acetic acid saturated with anhydrous hydrobromic acid. The mixture is cooled and poured over crushed ice and the solid collected. The crude material is recrystallized from ethanol and petroleum ether to give 1,1-bis(4-hydroxyphenyl)-1-phenyl-2,2,2-trifluoroethane.

Workup

  1. customThe mixture is then transferred to a separatory funnel
  2. washthe organic material is washed with water (3×11), saturated bicarbonate (3×500 ml) and water (2×500 ml)
  3. customThe organic phase is dried
  4. customthe volatiles removed in vacuo
  5. customThe resulting material is crystallized from aqueous methanol
  6. temperatureThe mixture is cooled
  7. additionpoured
  8. customover crushed ice
  9. customthe solid collected
  10. customThe crude material is recrystallized from ethanol and petroleum ether

Sources & evidence

ORD record
ord-7ba62443ec7649e18842d3f4e41dec27
Source dataset
uspto-grants-1993_09
Patent number
US05247050

Linked notes

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