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

HRID 46784
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HRID 46784 반응식
[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]
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참가 물질

5

반응물 3

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

생성물 1

HCID 128766212-(2',6'-Dichloro-4'-nitrophenyl)-5,5-dimethyl-1,3-cyclohexanedione수율 87.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
75 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d63744d14b7746e18374da3f92f30334
출처 데이터셋
uspto-grants-1979_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04175135

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