1,3-Cyclohexanedione → HCID 15077420, compound

HRID 1031326Notes

Reaction equation

HRID 1031326 reaction equation
C(=O)([O-])[O-].[K+].[K+].C1(N=C=NC2CCCCC2)CCCCC1.[Cl:22][C:23]1[C:31]([C:32]([O:34][CH3:35])=[O:33])=[C:30]([S:36]([CH3:39])(=[O:38])=[O:37])[CH:29]=[CH:28][C:24]=1[C:25]([OH:27])=O.[C:40]1(=[O:47])[CH2:45][CH2:44][CH2:43][C:42](=[O:46])[CH2:41]1>C(O)(CC)(C)C>[Cl:22][C:23]1[C:31]([C:32]([O:34][CH3:35])=[O:33])=[C:30]([S:36]([CH3:39])(=[O:38])=[O:37])[CH:29]=[CH:28][C:24]=1[C:25]([CH:41]1[C:42](=[O:46])[CH2:43][CH2:44][CH2:45][C:40]1=[O:47])=[O:27]

Participants

6

Reactant 4

HCID 104341,3-CyclohexanedioneHCID 10868DicyclohexylcarbodiimideHCID 11430Potassium CarbonateHCID 15132852HCID 15132852, compound

Product 1

HCID 15077420HCID 15077420, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent

Conditions

Temperature
80 °C

Procedure

0.28 g of potassium carbonate and 0.77 g of N,N'-dicyclohexylcarbodiimide were added to a solution mixture comprising 1.0 g of 2-chloro-4-methanesulfonyl-3-methoxycarbonyl benzoic acid, 0.38 g of 1,3-cyclohexane dione and 30 ml of t-amyl alcohol. The mixture was stirred at 80° C. for 3 hours. It was concentrated under reduced pressure, and an aqueous potassium carbonate solution was added thereto. Insoluble substances were removed by filtration. The filtrate was washed with chloroform, then acidified by an addition of concentrated hydrochloric acid and extracted with chloroform. The chloroform layer was washed with water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure to obtain a crude desired product. This crude product was crystallized from ethanol to obtain 0.3 g of the desired product. Melting point: 160-162° C.

Workup

  1. concentrationIt was concentrated under reduced pressure
  2. additionan aqueous potassium carbonate solution was added
  3. customInsoluble substances were removed by filtration
  4. washThe filtrate was washed with chloroform
  5. additionacidified by an addition of concentrated hydrochloric acid
  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. distillationThen, the solvent was distilled off under reduced pressure
  10. customto obtain a crude desired product
  11. customThis crude product was crystallized from ethanol

Sources & evidence

ORD record
ord-1d6306cf816e47df9afb5775076a68fa
Source dataset
uspto-grants-1990_09
Patent number
US04954165

Reaction notes

Loading…