Hydrochloric Acid → 1,2-Bis(4-chlorophenyl)ethanone

HRID 1863350Notes

Reaction equation

HRID 1863350 reaction equation
[Cl-:1].[Cl-].[Cl-].[Al+3].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13](Cl)=[O:14])=[CH:8][CH:7]=1.Cl>ClC1C=CC=CC=1>[Cl:1][C:6]1[CH:11]=[CH:10][C:9]([C:13](=[O:14])[CH2:12][C:9]2[CH:10]=[CH:11][C:6]([Cl:5])=[CH:7][CH:8]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 906924-Chlorophenylacetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5873181,2-Bis(4-chlorophenyl)ethanone

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

Aluminum trichloride (11.75 g.; 0.088 mole) was added portionwise to a stirred mixture of the p-chlorophenylacetyl chloride and chlorobenzene (30 ml.). Following addition, the mixture was allowed to stand for 24 hours. The resulting dark brown paste was scooped out and stirred into a slurry of ice and conc. hydrochloric acid which was then extracted with methylene chloride. The organic extracts were washed with 1 N hydrochloric acid, saturated sodium bicarbonate, saturated sodium chloride; dried over sodium sulfate and concentrated in vacuo. Recrystallization from methanol afforded 16.47 g. (71% yield), m.p. 111.5°-114° C.

Workup

  1. additionaddition
  2. extractionwas then extracted with methylene chloride
  3. washThe organic extracts were washed with 1 N hydrochloric acid, saturated sodium bicarbonate, saturated sodium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customRecrystallization from methanol
  7. customafforded 16.47 g

Sources & evidence

ORD record
ord-a046b4b46cbe44f9a250dc5f6e9c76c1
Source dataset
uspto-grants-1979_09
Patent number
US04168315

Reaction notes

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