Benzoic Acid → 2,4-Dimethylbenzophenone

HRID 505980Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505980
[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.CCCCN1C=[N+](C)C=C1>[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

5

Edukt 3

HCID 243Benzoic AcidHCID 7929M-XyleneHCID 27341621-Butyl-3-methylimidazolium

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-95eb8ff5d4f948f08e3012264a4f78c4
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781625B2

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