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Dichlone → HCID 178516332, compound

HRID 2061943
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Reaction equation

HRID 2061943 reaction equation
Cl[C:2]1[C:3](=[O:14])[C:4]2[C:9]([C:10](=[O:13])[C:11]=1[Cl:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C@H:22]2[CH2:27][CH2:26][C@H:25](C(O)=O)[CH2:24][CH2:23]2)=[CH:18][CH:17]=1.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+]>C(#N)C.O.[N+]([O-])([O-])=O.[Ag+]>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C@H:22]2[CH2:27][CH2:26][C@H:25]([C:2]3[C:3](=[O:14])[C:4]4[C:9]([C:10](=[O:13])[C:11]=3[Cl:12])=[CH:8][CH:7]=[CH:6][CH:5]=4)[CH2:24][CH2:23]2)=[CH:18][CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8342DichloneHCID 62648Ammonium PersulfateHCID 178525693HCID 178525693, compound

Product 1

HCID 178516332HCID 178516332, compoundYield 17.7%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalyst
HCID 962
Water
Solvent
HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,3-dichloro-1,4-naphthoquinone (5 gm), trans 4-(4-chlorophenyl)-cyclohexane-1-carboxylic acid (6.06 gm) and silver nitrate (2.47 gm) is taken in acetonitrile (60 ml) and the mixture is heated to reflux, maintaining good stirring. Then a solution of ammonium persulphate (14.23 gm) in water (77 ml) is added through a dropping funnel over a period of 1-2 hrs. The mixture refluxed for 4 hrs. Then it is cooled in ice for about 1 hr after which it is filtered. The solid is extracted with hot methylene chloride (100 ml×3). The organic layer is dried over anhydrous sodium sulphate and concentrated to get light brownish yellow solid. This on crystallization from acetonitrile afforded the trans compound as yellow crystals (1.5 gm).

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux
  3. temperaturemaintaining good stirring
  4. temperatureThe mixture refluxed for 4 hrs
  5. temperatureThen it is cooled in ice for about 1 hr after which it
  6. filtrationis filtered
  7. extractionThe solid is extracted with hot methylene chloride (100 ml×3)
  8. dry with materialThe organic layer is dried over anhydrous sodium sulphate
  9. concentrationconcentrated
  10. customto get light brownish yellow solid
  11. customThis on crystallization from acetonitrile

Sources & evidence

ORD record
ord-a047abe9920248ad859df6329d594396
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08283499B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes