2-Chloroanisole → 4-Methoxy-4'-methylbiphenyl

HRID 467244Notes

Reaction equation

HRID 467244 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4](S([O-])=O)=[CH:3][CH:2]=1.[Na+].Cl[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20].[O-2].[Ca+2]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN1CCCC1=O>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][C:17]([C:4]2[CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH:3]=2)=[CH:18][CH:13]=1

Participants

7

Reactant 3

HCID 130112-ChloroanisoleHCID 2723791Sodium p-toluenesulfinate2×HCID 6850728Calciumoxide

Product 1

HCID 17047594-Methoxy-4'-methylbiphenylYield 42.5%

Reagents, catalysts & solvents 3

HCID 742671,2-Bis(diphenylphosphino)ethaneCatalystHCID 167845palladium(II) acetateCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

3.56 g (20 mmol) of sodium p-toluenesulfinate, 2.85 g (20 mmol) of chloroanisole, 0.0225 g (0.1 mmol) of palladium acetate, 0.0478 g (0.12 mmol) of 1,2-bis(diphenylphosphino)-ethane, 3.37 g (60 mmol) calcium oxide and 60 ml of N-methyl-2-pyrrolidone were placed in a 100 ml round bottom flask and reacted at 150° C. in a nitrogen gas stream for 6 hours. After the completion of the reaction, the reaction mixture was analyzed by means to high performance liquid chromatography. The analysis showed that 46% of sodium p-toluenesulfinate was converted and 8.5 mmol (yield 42%) of 4'-methoxy-4-methylbiphenyl was formed in the reaction mixture solution.

Workup

  1. customreacted at 150° C. in a nitrogen gas stream for 6 hours
  2. customAfter the completion of the reaction

Sources & evidence

ORD record
ord-2882de0a8da445c69dcf118acfb1cfd6
Source dataset
uspto-grants-1992_10
Patent number
US05159082

Reaction notes

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