Hydrochloric Acid → 4-acetyl-4'-chlorobiphenyl

HRID 1703784Notes

Reaction equation

HRID 1703784 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[C:18](Cl)(=[O:20])[CH3:19].Cl>O.C(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[CH:14][CH:13]=2)=[CH:10][CH:11]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 163234-ChlorobiphenylHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5925694-acetyl-4'-chlorobiphenyl

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

To a cooled, stirred suspension containing 154 gms. of anhydrous aluminum chloride, 800 ml. of carbon tetrachloride and 200 gms of p-chlorobiphenyl add (dropwise) 91 gms of acetyl chloride. When the reaction temperature of the mixture reaches 10° C., add 60 ml of methylene chloride and allow the reaction mixture to slowly reach room temperature. Stir the mixture overnight. Pour the resulting mixture into 1 liter of crushed ice and water containing 100 ml. of conc. hydrochloric acid. Separate the organic phase, dry over anhydrous sulfate, filter, concentrate, and triturate the solid residue with 600 ml. of hexane to yield 1-(4'chloro[1,1']biphenyl-4-yl) ethanone, m.p. 100°-101° C.

Workup

  1. additioncontaining 154 gms
  2. customreaches 10° C.
  3. customto slowly reach room temperature
  4. stirringStir the mixture overnight
  5. customSeparate the organic phase
  6. dry with materialdry over anhydrous sulfate
  7. filtrationfilter
  8. concentrationconcentrate
  9. customtriturate the solid residue with 600 ml

Sources & evidence

ORD record
ord-4255119f6bc64bc48804a11220723827
Source dataset
uspto-grants-1978_11
Patent number
US04125612

Reaction notes

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