Potassium Carbonate → 2-(2',6'-Dichloro-4'-nitrophenyl)-5,5-dimethyl-1,3-cyclohexanedione

HRID 127826

Reaktionsgleichung

Reaktionsgleichung von HRID 127826
[CH3:1][C:2]1([CH3:10])[CH2:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[Cl:17][C:18]1[CH:19]=[C:20]([N+:26]([O-:28])=[O:27])[CH:21]=[C:22]([Cl:25])[C:23]=1Cl>CN(C)C=O>[Cl:17][C:18]1[CH:19]=[C:20]([N+:26]([O-:28])=[O:27])[CH:21]=[C:22]([Cl:25])[C:23]=1[CH:5]1[C:6](=[O:8])[CH2:7][C:2]([CH3:10])([CH3:1])[CH2:3][C:4]1=[O:9]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 31358DimedoneHCID 883653,4,5-Trichloronitrobenzene

Produkt 1

HCID 128766212-(2',6'-Dichloro-4'-nitrophenyl)-5,5-dimethyl-1,3-cyclohexanedioneAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A solution of 30.98 g (0.221 mol) of 5,5-dimethyl-1,3-cyclohexanedione and 76.36 g (0.553 mol) of anhydrous potassium carbonate in 300 ml of dimethylformamide was heated to 75° C. with stirring under N2 for one hour. The 3,4,5-trichloronitrobenzene (50.0 g, 0.221 mol) was dissolved in 100 ml of dimethylformamide and added to the reaction mixture, while stirring and maintaining the temperature at 75° C. A deep red-colored solution was formed, and when the addition was complete the temperature was raised to 100° C. and the mixture stirred over night at this temperature. Most of the dimethylformamide was removed by vacuum distillation, and 21 of water was added to the residue. The aqueous solution was extracted three times with 500 ml portions of benzene, then N2 was passed through the aqueous solution while warming to remove dissolved benzene. The solution was cooled in an ice bath and acidified with 6 N HCl to give 63.8 g (87%) of 2-(2',6'-dichloro-4'-nitrophenyl)-5,5-dimethyl-1,3-cyclohexanedione as a tan powder, m.p. 288°-290° C.

Aufarbeitung

  1. additionadded to the reaction mixture
  2. stirringwhile stirring
  3. customA deep red-colored solution was formed
  4. additionwhen the addition
  5. temperaturewas raised to 100° C.
  6. stirringthe mixture stirred over night at this temperature
  7. customMost of the dimethylformamide was removed by vacuum distillation, and 21 of water
  8. additionwas added to the residue
  9. extractionThe aqueous solution was extracted three times with 500 ml portions of benzene
  10. temperaturewhile warming
  11. customto remove
  12. dissolutiondissolved benzene
  13. temperatureThe solution was cooled in an ice bath

Quellen und Nachweise

ORD-Eintrag
ord-13bda6aa209747d582b748966dc65884
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04257858

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