p-Toluenesulfonic acid monohydrate → 1,1'-(Prop-1-ene-1,1-diyl)bis(4-fluorobenzene)

HRID 1282471Notes

Reaction equation

HRID 1282471 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)(O)[CH2:9][CH3:10])=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)=[CH:9][CH3:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 18424484HCID 18424484, compound

Product 1

HCID 184244971,1'-(Prop-1-ene-1,1-diyl)bis(4-fluorobenzene)Yield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Into a reactor were introduced 2.80 g (11.3 mmol) of the 1,1-bis(4-fluorophenyl)propanol, 60 mL of toluene, and 14 mg of p-toluenesulfonic acid monohydrate under a nitrogen atmosphere. Azeotropic dehydration was conducted for 1 hour with toluene refluxing. After being cooled, the reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution, subsequently dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 2.39 g (92%) of the target compound as white crystals.

Workup

  1. temperatureAfter being cooled
  2. washthe reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
  3. dry with materialsubsequently dried with anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-59803f55663c495981c236257284bf15
Source dataset
uspto-grants-2002_09
Patent number
US06455720B1

Reaction notes

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