Acetophenone → 1,1-Diphenylethylene

HRID 1459876Notes

Reaction equation

HRID 1459876 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=O)[CH3:10].C(OC(=O)C)(=O)C>C(O)(=O)C>[C:1]1([C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7410AcetophenoneHCID 7918Acetic AnhydrideHCID 178418255HCID 178418255, compound

Product 1

HCID 107401,1-Diphenylethylene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Crude DPE (Aldrich or from reaction of phenylmagnesium bromide with acetophenone, acetylation with acetic anhydride and thermal elimination of acetic acid) is distilled through a column having at least 50 theoretical plates (spinning-band column; a Sulzer packed column for larger amounts) to a purity of 99.8%. The usually slightly yellow distillate is filtered through a 20 cm Alox column (Woelm alumina for chromatography, anhydrous), titrated with 1.5N sec-butyllithium to a deep red color and distilled off over a simple still head under reduced pressure (1 mbar). The resulting product is completely colorless and can be used directly in the anionic polymerization.

Workup

  1. distillationis distilled through a column
  2. filtrationThe usually slightly yellow distillate is filtered through a 20 cm Alox column (Woelm alumina for chromatography, anhydrous)
  3. distillationdistilled off over a simple
  4. customcan be used directly in the anionic polymerization

Sources & evidence

ORD record
ord-c7f67e04c1d14a8e95c06ddfc2ec249b
Source dataset
uspto-grants-1998_12
Patent number
US05854353

Reaction notes

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