Benzoyl chloride → 2-benzoylcyclohexane-1,3-dione

HRID 324718Notes

Reaction equation

HRID 324718 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N1C=NC=N1>C(#N)C>[C:15]([CH:2]1[C:3](=[O:7])[CH2:4][CH2:5][CH2:6][C:1]1=[O:8])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 92571H-1,2,4-TriazoleHCID 104341,3-CyclohexanedioneHCID 11430Potassium Carbonate2×

Product 1

HCID 108568932-benzoylcyclohexane-1,3-dioneYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 1,3-Cyclohexanedione (2.31 g), potassium carbonate (1.5 g) and acetonitrile (20 ml) were stirred at 35° C. for 3 hrs. To the resulting suspension was added benzoylchloride (1.5 g) over a few minutes and the mixture was stirred for 30 minutes. Potassium carbonate (2 g) and 1,2,4-triazole (0.035 g) were then added and the mixture was stirred at 35° C. for 16 hrs. After this time the reaction mixture was evaporated under reduced pressure, the mixture dissolved in water and acidified with HCl to precipitate the product. Extraction into chloroform and evaporation gave a 90% yield of 2-benzoyl-1,3-cyclohexanedione.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. stirringthe mixture was stirred at 35° C. for 16 hrs
  3. customAfter this time the reaction mixture was evaporated under reduced pressure
  4. dissolutionthe mixture dissolved in water
  5. customto precipitate the product
  6. extractionExtraction
  7. custominto chloroform and evaporation

Sources & evidence

ORD record
ord-e91dfd397f694e4e9ddf740d96b95eaa
Source dataset
uspto-grants-2001_04
Patent number
US06218579B1

Reaction notes

Loading…