Alpha-Methylstyrene → 1,2-Diphenyl-1-propene

HRID 1156253Notes

Reaction equation

HRID 1156253 reaction equation
C(Cl)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH2:12].C(N(C)C)C1C=CC=CC=1>CC1C=CC(C)=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:12][C:11](=[CH:10][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 7407Alpha-MethylstyreneHCID 7412Benzoyl chlorideHCID 7681N,N-Dimethylbenzylamine

Product 1

HCID 130701,2-Diphenyl-1-propeneYield 3.3%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7809P-XyleneSolvent

Procedure

0.448 g (2 millimols) of palladium acetate, 28.11 g (0.2 mol) of benzoyl chloride, 23.64 g (0.2 mol) of α-methylstyrene and 27.04 g (0.2 mol) of N-benzyldimethylamine in 400 ml of p-xylene are stirred for 11 hours at 130° C. The mixture is extracted by shaking with 400 ml of 2 NHCl and 400 ml of 2 N NaOH and is then dried over magnesium sulfate. The crude product is chromatographed on silica gel in methylene chloride and subsequently recrystallised from n-pentane. 1.3 g (3% of theory) of α-methylstilbene are obtained as colourless crystals of melting point 79.0° C.

Workup

  1. extractionThe mixture is extracted
  2. dry with materialis then dried over magnesium sulfate
  3. customThe crude product is chromatographed on silica gel in methylene chloride
  4. customsubsequently recrystallised from n-pentane

Sources & evidence

ORD record
ord-265bbf29c37d43fc9302054311303cf3
Source dataset
uspto-grants-1982_06
Patent number
US04335055

Reaction notes

Loading…