Chlorobenzene → 4-Chlorophenyl cyclopropyl ketone

HRID 2164068Notes

Reaction equation

HRID 2164068 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].Cl[CH2:6][CH2:7][CH2:8][C:9](Cl)=[O:10].[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH:8]1([C:9]([C:16]2[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH:15]=2)=[O:10])[CH2:6][CH2:7]1

Participants

4

Reactant 3

HCID 7964Chlorobenzene2×HCID 783704-Chlorobutyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 811484-Chlorophenyl cyclopropyl ketone

Conditions

Temperature
12.5 °C

Procedure

A mixture of anhydrous aluminium chloride (20 g) and chlorobenzene (100 ml) was cooled to 10-15° C and treated dropwise with a solution of 4-chlorobutyrylchloride (20 g) in chlorobenzene (20 ml) over a period of 10 minutes with continuous stirring. The solution was warmed to 20-25° C and stirring was continued for a further 1 hour. It was poured onto ice and extracted with ether and the dried ethereal extract evaporated. The resulting liquid was treated with a solution of potassium hydroxide (12 g) in methanol (60 ml) and left to stand for 30 minutes with occasional shaking. After filtration the residue was washed with methanol and the filtrate evaporated to dryness. The oil was dissolved in ether and washed with water. The dried ethereal solution (Na2SO4) was evaporated and distilled (b.p.125-127°/5mm), yield =21.3 g,nD = 1.5700

Workup

  1. temperatureThe solution was warmed to 20-25° C
  2. additionIt was poured onto ice
  3. extractionextracted with ether
  4. extractionthe dried ethereal extract
  5. customevaporated
  6. additionThe resulting liquid was treated with a solution of potassium hydroxide (12 g) in methanol (60 ml)
  7. waitleft
  8. waitto stand for 30 minutes with occasional shaking
  9. filtrationAfter filtration the residue
  10. washwas washed with methanol
  11. customthe filtrate evaporated to dryness
  12. dissolutionThe oil was dissolved in ether
  13. washwashed with water
  14. customThe dried ethereal solution (Na2SO4) was evaporated
  15. distillationdistilled (b.p.125-127°/5mm)
  16. customyield =21.3 g,nD = 1.5700

Sources & evidence

ORD record
ord-352311c6a7e94b148f30d9233631cfef
Source dataset
uspto-grants-1979_01
Patent number
US04137324

Reaction notes

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