1-Methylcyclohexanecarboxylic acid → HCID 178421666, compound

HRID 1737147Notes

Reaction equation

HRID 1737147 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.[CH3:14][C:15]1(C(O)=O)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.S(O[O-])([O-])(=O)=O.[NH4+].[NH4+]>C(#N)C.O.C(OCC)C.[N+]([O-])([O-])=O.[Ag+]>[OH:1][C:2]1[C:3](=[O:13])[C:4]2[C:9]([C:10](=[O:12])[C:11]=1[C:15]1([CH3:14])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

8

Reactant 3

HCID 707441-Methylcyclohexanecarboxylic acidHCID 9855511Ammonium peroxysulphateHCID 178516607HCID 178516607, compound

Product 1

HCID 178421666HCID 178421666, compoundYield 19.2%

Reagents, catalysts & solvents 4

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 2-hydroxy-naphthalene-1,4-dione (1.00 g, 5.7 mmol), 1-methylcyclohexanecarboxylic acid (1.22 g, 8.6 mmol) and silver nitrate (600 mg) in a mixture of acetonitrile (20 ml) and water (20 ml) at 65° C. was slowly added a solution of ammonium peroxysulphate (1.96 g, 8.6 mmol) in water (10 ml) over a period of 15 minutes. The mixture was heated for a further hour before cooling to room temperature (about 20° C.) and diluting with diethyl ether (50 ml). The organic phase was separated and washed successively with water, dilute aqueous sodium hydrogen carbonate solution, water and saturated sodium chloride solution before drying over magnesium sulphate. Filtration and evaporation of the solvent under reduced pressure followed by silica gel column chromatography using 2:1 petrol:diethyl ether as eluant gave 2-hydroxy-3-(1-methyl-cyclohexyl)naphthalene-1,4-dione (296 mg) as a yellow crystalline compound, m.pt.: 79° C.

Workup

  1. temperatureThe mixture was heated for a further hour
  2. customThe organic phase was separated
  3. washwashed successively with water, dilute aqueous sodium hydrogen carbonate solution, water and saturated sodium chloride solution
  4. dry with materialbefore drying over magnesium sulphate
  5. filtrationFiltration and evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-1d1f8cc128424d1786d6f53d18583f6c
Source dataset
uspto-grants-1999_10
Patent number
US05962002

Reaction notes

Loading…