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

HRID 1957770Notes

Reaction equation

HRID 1957770 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-7f853938e56247f2aed89d4a91e0d8a1
Source dataset
uspto-grants-1998_07
Patent number
US05786513

Reaction notes

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