2-Chloro-1,4-naphthoquinone → 1,4-Naphthalenedione, 2-chloro-3-[cis-4-(4-chlorophenyl)cyclohexyl]-

HRID 1596425Notes

Reaction equation

HRID 1596425 reaction equation
[Cl:1][C:2]1[C:3](=[O:13])[C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[CH2:26][CH2:25][CH:24](C(O)=O)[CH2:23][CH2:22]2)=[CH:17][CH:16]=1.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+]>C(#N)C.O.[N+]([O-])([O-])=O.[Ag+]>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[CH2:26][CH2:25][CH:24]([C:11]3[C:10](=[O:12])[C:9]4[C:4]([C:3](=[O:13])[C:2]=3[Cl:1])=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH2:23][CH2:22]2)=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 138912-Chloro-1,4-naphthoquinoneHCID 62648Ammonium PersulfateHCID 27357924-(4-Chlorophenyl)cyclohexane-1-carboxylic acid

Product 1

HCID 111010701,4-Naphthalenedione, 2-chloro-3-[cis-4-(4-chlorophenyl)cyclohexyl]-Yield 35%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-chloro-1,4-naphthoquinone (3.95 g, 0.02 mol), 4-(4-chlorophenyl)cyclohexane-1-carboxylic acid (4.9 g, 0.02 mol) and powdered silver nitrate (1.05 g, 0.0062 mol) was heated to reflux with vigorous stirring in 40 ml of acetonitrile. A solution of ammonium persulphate (12.0 g, 0.0525 mol) in 50 ml of water was added dropwise over 1 hour. The mixture was refluxed for 3 hours then cooled in ice for 30 mins, after which it was filtered and the residual sticky solid extracted twice with boiling chloroform to remove inorganic material. The chloroform was removed by evaporation to leave a yellow-brown solid (ca 2.7 g). This was dissolved in 40 ml of boiling acetonitrile; a little insoluble material was removed by filtration. On cooling the title compound separated as yellow crystals, (550 mg) m.p. 172-175° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureThe mixture was refluxed for 3 hours
  4. temperaturethen cooled in ice for 30 mins
  5. filtrationafter which it was filtered
  6. extractionthe residual sticky solid extracted twice with boiling chloroform
  7. customto remove inorganic material
  8. customThe chloroform was removed by evaporation

Sources & evidence

ORD record
ord-968ae23aa0344e7fbf3fcfd418ed0cd1
Source dataset
uspto-grants-2001_09
Patent number
US06291488B1

Reaction notes

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