Chlorobenzene → 4-CHLOROPHENYL CYCLOHEXYL KETONE

HRID 1953264Notes

Reaction equation

HRID 1953264 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH:12]1([C:18](Cl)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>>[CH:12]1([C:18]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 3

HCID 7964ChlorobenzeneHCID 75938Cyclohexanecarbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 115794564-CHLOROPHENYL CYCLOHEXYL KETONE

Procedure

To a mixture of 80 ml (0.78 mol) of chlorobenzene and 30 g (0.22 mol) of aluminium chloride are added dropwise at 15-20° C. 24 ml (0.18 mol) of cyclohexanecarboxylic acid chloride. After one hour at ambient temperature the reaction mixture is heated for 5 hours to 50° C. After cooling, the mixture is then decomposed with ice water/conc. hydrochloric acid and the aqueous phase is extracted with methylene chloride. The combined organic extracts are dried and evaporated down. The residue is distilled under high vacuum (2 mm, 105-115° C.). The desired fraction is combined with water, the precipitate formed is suction filtered and dried.

Workup

  1. additionare added dropwise at 15-20° C
  2. temperatureAfter cooling
  3. extractionhydrochloric acid and the aqueous phase is extracted with methylene chloride
  4. customThe combined organic extracts are dried
  5. customevaporated down
  6. distillationThe residue is distilled under high vacuum (2 mm, 105-115° C.)
  7. customthe precipitate formed
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-099f75450912463a90087ed52bc32345
Source dataset
uspto-grants-2000_09
Patent number
US06114532

Reaction notes

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