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

HRID 1455860Notes

Reaction equation

HRID 1455860 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 65911,1,2,2-TetrachloroethaneSolvent

Procedure

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-tetrachloroethane, 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.

Workup

  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

Sources & evidence

ORD record
ord-02f59a759fdf44f58589e412cf2950bc
Source dataset
uspto-grants-1998_12
Patent number
US05843869

Reaction notes

Loading…