1,2-Dichloro-4-nitrobenzene → 2-(2'-Chloro-4'-nitrophenyl)-5,5-dimethyl-1,3-cyclohexandione

HRID 127529

Reaktionsgleichung

Reaktionsgleichung von HRID 127529
[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+:25]([O-:27])=[O:26])[CH:21]=[CH:22][C:23]=1Cl>CN(C)C=O>[Cl:17][C:18]1[CH:19]=[C:20]([N+:25]([O-:27])=[O:26])[CH:21]=[CH:22][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 74431,2-Dichloro-4-nitrobenzeneHCID 11430Potassium CarbonateHCID 31358Dimedone

Produkt 1

HCID 128766182-(2'-Chloro-4'-nitrophenyl)-5,5-dimethyl-1,3-cyclohexandioneAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A solution containing 42.05 g (0.300 mol) of 5,5-dimethyl-1,3-cyclohexanedione and 100 g (0.718 g-atom) of anhydrous potassium carbonate in 300 ml of dry dimethylformamide was heated to 75° C. under nitrogen and stirred for one hour. The 3,4-dichloronitrobenzene, 57.60 g (0.300 mol) was dissolved in 100 ml dimethylformamide and added dropwise to the reaction mixture while stirring and maintaining the temperature of the reaction mixture at 75° C. A deep red-colored solution formed, and when the addition was complete the reaction temperature was raised to 100° C. and held at this temperature for 3 hours. Most of the dimethylformamide was removed by vacuum distillation. The residue was poured into 21 of ice water and extracted three times with 500 ml of benzene. Nitrogen was then passed through the aqueous solution while warming to remove dissolved benzene. The aqueous solution was cooled in an ice bath and acidified to give a tacky precipitate, which, upon warming solidified and was collected by suction filtration. The product was recrystallized from acetone to give 31.7 g (36%) of 2-(2'-Chloro-4'-nitrophenyl)-5,5-dimethyl-1,3-cyclohexanedione as a white powder, m.p. 250°-253° C.

Aufarbeitung

  1. additionadded dropwise to the reaction mixture
  2. stirringwhile stirring
  3. temperaturemaintaining the temperature of the reaction mixture at 75° C
  4. customA deep red-colored solution formed
  5. additionwhen the addition
  6. temperaturewas raised to 100° C.
  7. waitheld at this temperature for 3 hours
  8. customMost of the dimethylformamide was removed by vacuum distillation
  9. additionThe residue was poured into 21 of ice water
  10. extractionextracted three times with 500 ml of benzene
  11. temperaturewhile warming
  12. customto remove
  13. dissolutiondissolved benzene
  14. temperatureThe aqueous solution was cooled in an ice bath
  15. customto give a tacky precipitate, which
  16. temperatureupon warming solidified
  17. filtrationwas collected by suction filtration
  18. customThe product was recrystallized from acetone

Quellen und Nachweise

ORD-Eintrag
ord-0ac3982872f44a96a252d155ee6d5a1a
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04256658

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