Benzoic Acid → 2,4-Dimethylbenzophenone

HRID 890851

Reaction equation

HRID 890851 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]1([CH3:17])[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[CH:11]=1>[Zn]>[CH3:17][C:10]1[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][C:15]=1[C:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:9]

Participants

4

Reactant 2

HCID 243Benzoic AcidHCID 7929M-Xylene

Product 1

HCID 708312,4-Dimethylbenzophenone

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

Benzoic acid (0.31 g, 2.5 mmol), m-xylene (0.53 g, 5.0 mmol), [bmim][NTf2] (0.50 g) and M(NTf2)2 (M=Co (0.14 g, 0.25 mmol), or Zn (0.15 g, 0.25 mmol) were placed in flasks equipped with stirrers and condensers. The contents of the flask were heated under reflux (ca 140-150 ° C.) for 2 days, then cooled to room temperature. The products were analysed by gas chromatographic analysis and found to give 93 and 87% conversions (for Co and Zn bis-triflimide reactions respectively) to 2,4-dimethylbenzophenone and, it is believed to be, 2,6-dimethylbenzophenone (11:1 isomer ratio in both cases). The results show that zinc and cobalt bis-triflimide have been found to catalyse the benzoylation of m-xylene with benzoic acid. The reaction is slower that the corresponding reaction with benzoyl chloride. The catalyst was recycled and the reaction was repeated. The results of the repeat experiment are shown in Table 4.

Workup

  1. customequipped with stirrers and condensers
  2. temperatureThe contents of the flask were heated
  3. temperatureunder reflux (ca 140-150 ° C.) for 2 days

Sources & evidence

ORD record
ord-e0bda77d3b5e4ee2ba250b316c832578
Source dataset
uspto-grants-2006_02
Patent number
US06998497B2

Linked notes

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