Benzophenone → Triphenylethylene

HRID 1282464Notes

Reaction equation

HRID 1282464 reaction equation
[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[C:11]1([C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 3102BenzophenoneHCID 178418336HCID 178418336, compound

Product 1

HCID 6025Triphenylethylene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Into a reactor was introduced 41 mL (55 mmol; 1.06 M THF solution) of benzylmagnesium chloride under a nitrogen atmosphere. The contents were cooled to 0° C. Thereafter, a solution prepared by mixing 9.11 g (50.0 mmol) of benzophenone with 18 mL of THF was gradually added dropwise thereto, and this mixture was stirred at room temperature for 1 hour. The resultant reaction mixture was washed with 0.1 M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, and saturated aqueous sodium chloride solution and then dried with anhydrous magnesium sulfate. Thereafter, the solvent was removed under reduced pressure. The concentrate was dissolved in 46 mL of toluene, and 0.18 g of p-toluenesulfonic acid monohydrate was added thereto. 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 12.5 g (98%) of a transparent oily substance.

Workup

  1. customThereafter, a solution prepared
  2. additionwas gradually added dropwise
  3. customThe resultant reaction mixture
  4. washwas washed with 0.1 M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, and saturated aqueous sodium chloride solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThereafter, the solvent was removed under reduced pressure
  7. dissolutionThe concentrate was dissolved in 46 mL of toluene
  8. addition0.18 g of p-toluenesulfonic acid monohydrate was added
  9. waitAzeotropic dehydration was conducted for 2 hours with toluene refluxing
  10. temperatureAfter being cooled
  11. washthe reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
  12. dry with materialsubsequently dried with anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customto obtain 12.5 g (98%) of a transparent oily substance

Sources & evidence

ORD record
ord-0556b497ced84a14807a919cf1eb760c
Source dataset
uspto-grants-2002_09
Patent number
US06455720B1

Reaction notes

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