Cyclohexanecarboxylic acid → HCID 178516880, compound

HRID 2061945Notes

Reaction equation

HRID 2061945 reaction equation
Cl[C:2]1[C:3](=[O:14])[C:4]2[C:9]([C:10](=[O:13])[C:11]=1Cl)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH:15]1(C(O)=O)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.S(OOS([O-])(=O)=O)([O-])(=O)=[O:25].[NH4+].[NH4+]>C(#N)C.O.[N+]([O-])([O-])=O.[Ag+]>[CH:15]1([C:2]2[C:3](=[O:14])[C:4]3[C:9]([C:10](=[O:13])[C:11]=2[OH:25])=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

7

Reactant 3

HCID 7413Cyclohexanecarboxylic acidHCID 8342DichloneHCID 62648Ammonium Persulfate

Product 1

HCID 178516880HCID 178516880, compoundYield 45.2%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,3-dichloro-1,4-naphthoquinone (5gm), cyclohexane carboxylic acid (2.7629 gm) and silver nitrate (2.095 gm) is taken in acetonitrile (60 ml) and the mixture is heated to reflux. Then a solution of ammonium persulphate (12.06 gm) in 77 ml of water is added through a dropping funnel over a period of 1 to 2 hrs. The mixture is refluxed for 4 hrs and cooled in ice for about 1 hr after which it is filtered. Filtrate is kept aside for acetonitrile recovery. The solid is extracted with hot methylene chloride (100 ml×3). Inorganics is kept aside for silver nitrate regeneration. The methylene chloride layer is dried over anhydrous sodium sulphate, concentrated to get light brownish yellow solid. This on crystallization from acetonitrile afforded the title compound as yellow crystals (2.5 gm). 300 MHz NMR of the compound fully agreed with the desired compound

Workup

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

Sources & evidence

ORD record
ord-6aa239f56c8d47eeb6c5dbe495a0aa80
Source dataset
uspto-grants-2012_10
Patent number
US08283499B2

Reaction notes

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