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

HRID 703143
Notes
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Reaction equation

HRID 703143 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 Nitrate
Catalyst
HCID 962WaterSolvent
HCID 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 the 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.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureThe mixture was refluxed for 3 hours the
  4. temperaturecooled 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-19c70a89ebce40fb8dafee85e0c5c210
Source dataset
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04981874

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes