Dichlone → HCID 178516332, compound

HRID 2061944Notes

Reaction equation

HRID 2061944 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]([CH:22]2[CH2:27][CH2:26][CH: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

Participants

7

Reactant 3

HCID 8342DichloneHCID 62648Ammonium PersulfateHCID 27357924-(4-Chlorophenyl)cyclohexane-1-carboxylic acid

Product 1

HCID 178516332HCID 178516332, compoundYield 39.8%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,3-dichloro-1,4-naphthoquinone (57.0 gm), 4-(4-chlorophenyl)-cyclohexane-1-carboxylic acid (60.0 gm) and silver nitrate (42.7 gm) is taken in acetonitrile (600 ml) and then a solution of ammonium persulphate (180.12 gm) in water (780 ml) is added. The mixture is heated to reflux, maintaining good stirring. The mixture was refluxed for 4 hrs. Then cooled in ice for about 1 hr after which it is filtered. The filtrate is kept aside for acetonitrile recovery. The solid is extracted with hot methylene chloride (100 ml×3). The inorganic salt is collected separately for recovery of silver. The organic layer is dried over anhydrous sodium sulphate and concentrated to get light brownish yellow solid (38.5 gm).

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. temperaturemaintaining good stirring
  4. temperatureThe mixture was refluxed for 4 hrs
  5. temperatureThen 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. customThe inorganic salt is collected separately for recovery of silver
  9. dry with materialThe organic layer is dried over anhydrous sodium sulphate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-734842e13652449a97843cf9ccbad59d
Source dataset
uspto-grants-2012_10
Patent number
US08283499B2

Reaction notes

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