Hydrochloric Acid → 2'-Chloro-2-methoxy-5-methyl-5'-nitrobenzophenone

HRID 428385Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 428385
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1.[Cl:14][C:15]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:16]=1[C:17](Cl)=[O:18].Cl>C(Cl)Cl>[Cl:14][C:15]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:16]=1[C:17](=[O:18])[C:8]1[CH:7]=[C:6]([CH3:5])[CH:11]=[CH:10][C:9]=1[O:12][CH3:13]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 77314-MethylanisoleHCID 117637Benzoyl chloride, 2-chloro-5-nitro-HCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 183144782'-Chloro-2-methoxy-5-methyl-5'-nitrobenzophenone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

A mixture of aluminum chloride (33.3 g, 25.0 mmol) in methylene chloride is cooled to about 5° C., treated over one hour with p-methylanisole (31.6 g, 25.0 mmol) while maintaining the reaction mixture temperature below 10° C., treated over 20 minutes with a solution of 2-chloro-5-nitrobenzoyl chloride (50.0 g, 22.7 mmol) in methylene chloride while maintaining the reaction mixture temperature below 10° C., warmed to and stirred at room temperature for 60 minutes, and poured onto ice. The resultant aqueous mixture is treated with concentrated hydrochloric acid (50 mL) and extracted with methylene chloride. The organic extract is dried over anhydrous magnesium sulfate and concentrated in vacuo to give a yellow solid. After placing the solid in a Kugelrohr apparatus at 40° C. to remove residual p-methylanisole, the title product is obtained as a beige solid (68.8 g, 99.1%) which is identified by NMR spectral analyses.

Aufarbeitung

  1. temperaturewhile maintaining the reaction mixture temperature below 10° C.
  2. temperaturewhile maintaining the reaction mixture temperature below 10° C.
  3. temperaturewarmed to and
  4. additionpoured onto ice
  5. extractionextracted with methylene chloride
  6. extractionThe organic extract
  7. dry with materialis dried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give a yellow solid
  10. customat 40° C.
  11. customto remove residual p-methylanisole

Quellen und Nachweise

ORD-Eintrag
ord-1b1ff2e7d2234a389dc2d81305bef15c
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313295B1

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