P-Toluic Acid → (4-Methoxyphenyl)(4-methylphenyl)methanone

HRID 279697

Reaktionsgleichung

Reaktionsgleichung von HRID 279697
FC(F)(F)S([O-])(=O)=O.[Pr+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.FC(F)(F)S(O)(=O)=O.[C:34]1([O:40][CH3:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[C:42]1([CH3:51])[CH:47]=[CH:46][C:45]([C:48](O)=[O:49])=[CH:44][CH:43]=1>C1(C)C=CC=CC=1.O>[CH3:41][O:40][C:34]1[CH:39]=[CH:38][C:37]([C:48]([C:45]2[CH:46]=[CH:47][C:42]([CH3:51])=[CH:43][CH:44]=2)=[O:49])=[CH:36][CH:35]=1

Komponenten

7

Edukt 4

HCID 7470P-Toluic AcidHCID 7519AnisoleHCID 62406Trifluoromethanesulfonic acidHCID 9894708Praseodymium(III) trifluoromethanesulfonate

Produkt 1

HCID 32113(4-Methoxyphenyl)(4-methylphenyl)methanoneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Praseodymium (III) trifluoromethanesulfonate (1.18 g as a wet solid), trifluoromethanesulfonic acid (0.30 g), anisole (2.38 g) and para-toluic acid (2.72 g) were refluxed together in 175 mL toluene with azeotropic removal of the lower water layer (Dean-Stark apparatus). After 22 hours, the mixture was cooled and extracted with 3×25 mL water, then by 2×25 mL saturated sodium bicarbonate solution. The organic layer was dried using anhydrous sodium sulfate, filtered, then concentrated down in vacuo to give crude 4-methoxy-4′-methylbenzophenone (2.7 g, 60% yield) as a cream-colored crystalline solid.

Aufarbeitung

  1. temperaturethe mixture was cooled
  2. extractionextracted with 3×25 mL water
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated down in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e10a51f8067e4e7f92269219d2b85cb0
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362375B1

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