Potassium Iodide → 2-Benzoyl-8-[2-chloro-4-methoxyphenoxy]-1-phenyl-1-octanone

HRID 426787Notes

Reaction equation

HRID 426787 reaction equation
[C:1]([CH2:9][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:20]=1[O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(=O)CC>[C:10]([CH:9]([CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][O:21][C:20]1[CH:29]=[CH:30][C:31]([O:33][CH3:34])=[CH:32][C:19]=1[Cl:18])[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:8])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8433DibenzoylmethaneHCID 11430Potassium CarbonateHCID 920684-((6-Bromohexyl)oxy)-3-chloroanisole

Product 1

HCID 127337272-Benzoyl-8-[2-chloro-4-methoxyphenoxy]-1-phenyl-1-octanoneYield 38.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 11.2 g (0.05 m) of dibenzoylmethane, 16.1 g (0.05 m) of 6-(2-chloro-4-methoxyphenoxy)hexyl bromide, 20.6 g (0.15 m) of milled potassium carbonate, 2.0 g of potassium iodide and 250 ml of 2-butanone was heated at reflux for 18 hours. The reaction mixture was filtered hot and concentrated to a brown oil. The latter was stirred with cold ether and seeded with a sample of the desired product having the m.p. 69°-70° C. The solid product thus obtained was collected to afford 9.0 g of 2-benzoyl-8-[2-chloro-4-methoxyphenoxy]-1-phenyl-1-octanone; MIC=3 microg/ml (herpes 2).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. filtrationThe reaction mixture was filtered hot
  4. concentrationconcentrated to a brown oil
  5. customThe solid product thus obtained
  6. customwas collected

Sources & evidence

ORD record
ord-0b8a365921ab421d991e7675692da256
Source dataset
uspto-grants-1979_10
Patent number
US04171365

Reaction notes

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