Benzoic Acid → 2,4-Dimethylbenzophenone

HRID 890851

Reaktionsgleichung

Reaktionsgleichung von HRID 890851
[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]

Komponenten

4

Edukt 2

HCID 243Benzoic AcidHCID 7929M-Xylene

Produkt 1

HCID 708312,4-Dimethylbenzophenone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23994ZincKatalysator

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-e0bda77d3b5e4ee2ba250b316c832578
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US06998497B2

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