Water → Di-p-tolyl

HRID 1154726Notes

Reaction equation

HRID 1154726 reaction equation
Cl([O-])(=O)(=O)=O.[C:6]([O-])(=O)[CH3:7].[C:10]1([CH3:17])[CH:15]=[CH:14][C:13]([Tl+2])=[CH:12][CH:11]=1.O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC=CC=1>[CH3:17][C:10]1[CH:15]=[CH:14][C:13]([C:10]2[CH:15]=[CH:14][C:6]([CH3:7])=[CH:12][CH:11]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 962WaterHCID 178475864HCID 178475864, compound

Product 1

HCID 11941Di-p-tolyl

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 241BenzeneSolvent

Procedure

A solution of 1000 parts by weight of p-tolyl thallium acetate perchlorate (p-CH3C6H4TlClO4CH3COO) in 6000 parts by weight of water and a solution of 2 parts by weight of palladium (II)-acetate [Pd(OAc)2 ] in 1500 parts by weight of benzene were stirred together vigorously for 2 hours at 60° C. Then the organic phase was separated and the benzene was distilled off under reduced pressure. 310 parts by weight of a residue remained which contained 297 parts by weight of p-tolyl acetate and 11 parts by weight of 4,4-dimethyl biphenyl in addition to palladium compounds. The reaction rate was 99% with a selectivity of 95%. The mixture was rectified over a short column at 10 m bar with the fraction passing over between 79° and 85° C. consisting of pure p-tolyl acetate. The distillation residue was taken up in acetone, and 4,4'-dimethyl biphenyl in pure form was obtained by addition of water.

Workup

  1. customThen the organic phase was separated
  2. distillationthe benzene was distilled off under reduced pressure
  3. additionin addition to palladium compounds
  4. custompassing over between 79° and 85° C.

Sources & evidence

ORD record
ord-d23e82b24bf746e8a75b39582014455d
Source dataset
uspto-grants-1984_12
Patent number
US04490552

Reaction notes

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