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

HRID 65275

反応式

HRID 65275 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+: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]

参加物

5

反応物 3

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

生成物 1

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

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 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 6N 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.

後処理

  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

出典と根拠

ORDレコード
ord-042d452852e245d9b28691cd445f1ad9
出典データセット
uspto-grants-1986_09
特許番号
US04613617

関連ノート

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