Hydrochloric Acid → 2,5'-Dichloro-2'-hydroxy-3'-methyl-4-methylsulfonylbenzophenone

HRID 1268418Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1268418
[Cl:1][C:2]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([CH3:23])[CH:17]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClC(Cl)C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([C:20]1[CH:21]=[C:16]([Cl:15])[CH:17]=[C:18]([CH3:23])[C:19]=1[OH:22])=[O:5]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 148554-Chloro-2-methylphenolHCID 6451240Aluminum(III) ChlorideHCID 11128804Benzoyl chloride, 2-chloro-4-(methylsulfonyl)-

Produkt 1

HCID 185446372,5'-Dichloro-2'-hydroxy-3'-methyl-4-methylsulfonylbenzophenoneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 65911,1,2,2-TetrachloroethaneLösungsmittel

Versuchsvorschrift

5.06 g of 2-chloro-4-methylsulfonylbenzoyl chloride are added in portions at room temperature to a mixture of 2.85 g of 4-chloro-2-methylphenol and 5.40 g of aluminum chloride in 100 ml of 1,1,2,2-tetra chloroethane, and the mixture is subsequently refluxed for 7 hours. When cold, the reaction mixture is poured onto 200 g of ice and 500 ml of concentrated hydrochloric acid. The organic phase is separated off, and the aqueous phase is extracted twice using 50 ml of dichloromethane. The combined organic phases are washed until neutral, dried over magnesium sulfate and evaporated. Recrystallization from a mixture of ethyl acetate and diisopropyl ether gives 4.2 g (60% of theory) of 2,5′-dichloro-2′-hydroxy-3′-methyl-4-methylsulfonylbenzophenone in the form of colorless crystals with a melting point of 175-180° C.

Aufarbeitung

  1. temperaturethe mixture is subsequently refluxed for 7 hours
  2. customThe organic phase is separated off
  3. extractionthe aqueous phase is extracted twice
  4. washThe combined organic phases are washed until neutral,
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customRecrystallization
  8. additionfrom a mixture of ethyl acetate and diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-e372c76e0b6848b8a4010ae93b1568ea
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06555714B1

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