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

HRID 65272

反応式

HRID 65272 の反応式
[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]

参加物

5

反応物 3

HCID 74431,2-Dichloro-4-nitrobenzeneHCID 11430Potassium CarbonateHCID 31358Dimedone

生成物 1

HCID 128766182-(2'-Chloro-4'-nitrophenyl)-5,5-dimethyl-1,3-cyclohexandione

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
75 °C

実験手順

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%) or 2-(2'-Chloro-4'-nitrophenyl)-5,5-dimethyl-1,3-cyclohexandione as a white powder, m.p. 250°-253° C.

後処理

  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

出典と根拠

ORDレコード
ord-11674178d09e4b1eb604e9ff3b49dfb8
出典データセット
uspto-grants-1986_09
特許番号
US04613617

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