4-(3,4-Dichlorophenyl)-3-buten-2-one → 5-(3,4-dichlorophenyl)cyclohexane-1,3-dione

HRID 1578081Notes

Reaction equation

HRID 1578081 reaction equation
[Na].C([C:4](CC)(C([O-])=O)[C:5]([O-])=[O:6])C.[Cl:13][C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH:17]=[CH:18][C:19](=[O:21])[CH3:20]>C(O)C>[Cl:13][C:14]1[CH:15]=[C:16]([CH:17]2[CH2:4][C:5](=[O:6])[CH2:20][C:19](=[O:21])[CH2:18]2)[CH:22]=[CH:23][C:24]=1[Cl:25]

Participants

5

Reactant 3

HCID 3265634-(3,4-Dichlorophenyl)-3-buten-2-oneHCID 5360545SodiumHCID 69515632,2-Diethylpropanedioate

Product 1

HCID 5991265-(3,4-dichlorophenyl)cyclohexane-1,3-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.3 g of sodium metal in 30 ml of ethanol is treated with 9 g of diethylmalonate and an ethanolic solution of 12.1 g of 3,4-dichlorobenzalacetone, heated under reflux for 15 min, cooled and concentrated to dryness in vacuo. The residue is treated with 400 ml of water containing 7 g of 80% potassium hydroxide pellets and heated under reflux for 2 hr. Insoluble material is removed and the filtrate is acidified with concentrated sulfuric acid, heated under reflux until carbon dioxide evolution ceases, cooled, filtered, washed with water and dried. Recrystallization from 2-propanol gives 5-(3,4-dichlorophenyl)-1,3-cyclohexanedione; mp 198°-200° C.

Workup

  1. temperatureunder reflux for 15 min
  2. temperaturecooled
  3. concentrationconcentrated to dryness in vacuo
  4. additionThe residue is treated with 400 ml of water containing 7 g of 80% potassium hydroxide pellets
  5. temperatureheated
  6. temperatureunder reflux for 2 hr
  7. customInsoluble material is removed
  8. temperatureheated
  9. temperatureunder reflux until carbon dioxide evolution ceases
  10. temperaturecooled
  11. filtrationfiltered
  12. washwashed with water
  13. customdried
  14. customRecrystallization from 2-propanol

Sources & evidence

ORD record
ord-4a9944c93b414ece8b51d84dca03b076
Source dataset
uspto-grants-1981_09
Patent number
US04291034

Reaction notes

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