1,3-Cyclohexanedione → HCID 14721240, compound

HRID 2371656Notes

Reaction equation

HRID 2371656 reaction equation
C(=O)([O-])[O-].[K+].[K+].C1(N=C=NC2CCCCC2)CCCCC1.[CH3:22][S:23]([C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=O)=[C:28]([CH3:35])[C:27]=1[CH2:36][O:37][CH3:38])(=[O:25])=[O:24].[C:39]1(=[O:46])[CH2:44][CH2:43][CH2:42][C:41](=[O:45])[CH2:40]1>C(O)(CC)(C)C>[CH3:22][S:23]([C:26]1[CH:34]=[CH:33][C:29]([C:30]([CH:40]2[C:41](=[O:45])[CH2:42][CH2:43][CH2:44][C:39]2=[O:46])=[O:32])=[C:28]([CH3:35])[C:27]=1[CH2:36][O:37][CH3:38])(=[O:24])=[O:25]

Participants

6

Reactant 4

HCID 104341,3-CyclohexanedioneHCID 10868DicyclohexylcarbodiimideHCID 11430Potassium CarbonateHCID 14721238HCID 14721238, compound

Product 1

HCID 14721240HCID 14721240, compoundYield 7.3%

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent

Conditions

Temperature
80 °C

Procedure

1.3 g of potassium carbonate and 3.0 g of N,N'-dicyclohexylcarbodiimide were added to a solution mixture comprising 2.0 g of 4-methanesulfonyl-3-methoxymethyl-2-methylbenzoic acid, 0.9 g of 1,3-cyclohexanedione and 100 ml of t-amyl alcohol. The mixture was stirred at 80° C. for 11 hours. It was concentrated under reduced pressure, and then an aqueous potassium carbonate solution was added. Then, insoluble substances were removed by filtration. The filtrate was washed with chloroform, then acidifed by an addition of concentrated hydrochloric and extracted with chloroform. The chloroform layer was washed with water and with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 1.1 g of a crude desired product. This crude product was recrystallized from ethanol to obtain 0.2 g of the desired product. Melting point: 192°-198° C.

Workup

  1. concentrationIt was concentrated under reduced pressure
  2. additionan aqueous potassium carbonate solution was added
  3. customThen, insoluble substances were removed by filtration
  4. washThe filtrate was washed with chloroform
  5. additionacidifed by an addition of concentrated hydrochloric and
  6. extractionextracted with chloroform
  7. washThe chloroform layer was washed with water and with a saturated sodium chloride aqueous solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customto obtain 1.1 g of a crude desired product
  11. customThis crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-e918176c73014ec99888157fc029947d
Source dataset
uspto-grants-1992_03
Patent number
US05094685

Reaction notes

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