Hydrochloric Acid → HCID 18544636, compound

HRID 1268419Notes

Reaction equation

HRID 1268419 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].[Al+3].[Cl-].[Cl-].Cl.Cl[CH:21]([Cl:25])[CH:22](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:3]1[C:4]([OH:5])=[CH:22][C:21]([Cl:25])=[CH:10][C:2]=1[Cl:15])=[O:5]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 65911,1,2,2-TetrachloroethaneHCID 6451240Aluminum(III) ChlorideHCID 11128804Benzoyl chloride, 2-chloro-4-(methylsulfonyl)-

Product 1

HCID 18544636HCID 18544636, compound

Procedure

3.00 g of 2-chloro-4-methylsulfonylbenzoyl chloride are added in portions at room temperature to a mixture of 1.97 g of 3,5-dichlorophenone and 3.23 g of aluminum chloride in 50 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 100 g of ice and 20 ml of concentrated hydrochloric acid. The organic phase is removed, and the aqueous phase is extracted twice using 50 ml of dichloromethane. The combined organic phases are washed until neutral and subsequently extracted three times using in each case 25 ml of 2 N sodium hydroxide solution. The combined alkaline extracts are brought to a pH of 2 using concentrated hydrochloric acid. The precipitate is filtered off, washed with water until neutral and dried. This gives 3.194 g (70% of theory) of 2,2′,4′-trichloro-6′-hydroxy-4-methylsulfonylbenzophenone in the form of colorless crystals with a melting point of 123-126° C.

Workup

  1. temperaturethe mixture is subsequently refluxed for 7 hours
  2. customThe organic phase is removed
  3. extractionthe aqueous phase is extracted twice
  4. washThe combined organic phases are washed until neutral and
  5. extractionsubsequently extracted three times
  6. filtrationThe precipitate is filtered off
  7. washwashed with water until neutral and
  8. customdried

Sources & evidence

ORD record
ord-92bee5afc9cb46c6933154ed5ec5ca72
Source dataset
uspto-grants-2003_04
Patent number
US06555714B1

Reaction notes

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