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

HRID 1282467Notes

Reaction equation

HRID 1282467 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)(O)[CH2:10][CH3:11])=[CH:5][CH:4]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:20][O:19][C:16]1[CH:15]=[CH:14][C:13]([C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[CH:10][CH3:11])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 18424508α-Ethyl-4-methoxy-α-(4-methoxyphenyl)benzenemethanol

Product 1

HCID 2523441,1'-(Prop-1-ene-1,1-diyl)bis(4-methoxybenzene)Yield 97.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Into a reactor were introduced 2.86 g (10.5 mmol) of the 1,1-bis(4-methoxyphenyl)propanol, 40 mL of toluene, and 28 mg of p-toluenesulfonic acid monohydrate under a nitrogen atmosphere. Azeotropic dehydration was conducted for 2 hours 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 2.60 g (97%) of the target compound as light-yellow 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-42f271a80cd84afc8b60ce0853b92086
Source dataset
uspto-grants-2002_09
Patent number
US06455720B1

Reaction notes

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