Cyclohexanecarboxylic acid → HCID 178516880, compound

HRID 1637969Notes

Reaction equation

HRID 1637969 reaction equation
[OH: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.[CH:14]1(C(O)=O)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+]>C(#N)C.O.[N+]([O-])([O-])=O.[Ag+]>[CH:14]1([C:11]2[C:10](=[O:12])[C:9]3[C:4]([C:3](=[O:13])[C:2]=2[OH:1])=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

7

Reactant 3

HCID 7413Cyclohexanecarboxylic acidHCID 62648Ammonium PersulfateHCID 178516607HCID 178516607, compound

Product 1

HCID 178516880HCID 178516880, compoundYield 24.7%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent3×HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-hydroxynaphthalene-1,4-dione (1.00 g, 5.74 mmol), cyclohexane carboxylic acid (1.10 g, 8.61 rnmol) and silver nitrate (520 mg) in acetonitrile (15 ml) and water (20 ml) heated at 65-70° C. was added an aqueous solution of ammonium persulphate (1.77 g, 7.77 mmol) in water (10 ml). After heating for 1 hour the mixture was cooled, diluted with water (50 ml) and extracted with ether (3×40 ml). The combined ether fractions were washed with water (3×25ml), saturated sodium chloride solution (25 ml) and dried over magnesium sulphate. Filtration and evaporation of solvents under reduced pressure and silica gel chromatography yielded the title compound (364 mg, m.p. 133° C.). This compound is listed as compound 12 in the Tables below.

Workup

  1. temperatureAfter heating for 1 hour the mixture
  2. temperaturewas cooled
  3. extractionextracted with ether (3×40 ml)
  4. washThe combined ether fractions were washed with water (3×25ml), saturated sodium chloride solution (25 ml)
  5. dry with materialdried over magnesium sulphate
  6. filtrationFiltration and evaporation of solvents under reduced pressure and silica gel chromatography

Sources & evidence

ORD record
ord-2c61ce0401ce471a97d0b9207924d34f
Source dataset
uspto-grants-2000_03
Patent number
US06043286

Reaction notes

Loading…