Water → 4-Chloro-2,2-dimethyl-2,3-dihydro-1H-inden-1-one

HRID 5777

反応式

HRID 5777 の反応式
[OH-].[K+].[Cl:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][C:8]2=O.[CH3:14]I.O.CN(C)[CH:19]=[O:20]>>[CH3:14][C:7]1([CH3:8])[CH2:6][C:5]2[C:9](=[CH:10][CH:11]=[CH:12][C:4]=2[Cl:3])[C:19]1=[O:20]

参加物

6

反応物 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodide2 回HCID 14797Potassium HydroxideHCID 113326814-chloro-2,3-dihydro-1H-inden-1-one

生成物 1

HCID 197941174-Chloro-2,2-dimethyl-2,3-dihydro-1H-inden-1-one

実験手順

22.4 g of pulverized potassium hydroxide and 0.1 g of 18-dibenzocrown-6 are added portionwise to a solution of 25 g of 4-chloroindanone and 56.7 g of methyl iodide in 120 ml of dimethylformamide in such a manner that the temperature is kept below +70° C. When the exothermic reaction is over, 5.6 g of methyl iodide are added and the mixture is agitated for another 0.5 hours. 200 ml of cold water are added and the mixture is extracted with diethyl ether. The organic phase is dried, with sodium sulfate and concentrated to dryness, affording 27.4 g of crude 2,2-dimethyl-4-chloro-indanone. This crude product is directly subjected to the Leuckart-Wallach amine preparation as described in "Organic Reactions vol. 5, page 301ff, John Wiley & Sons, New York 1949", yielding pure 1-amino-4-chloro-2,2-dimethyl-indane.

後処理

  1. customis kept below +70° C
  2. customWhen the exothermic reaction
  3. additionare added
  4. extractionthe mixture is extracted with diethyl ether
  5. dry with materialThe organic phase is dried, with sodium sulfate
  6. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-65d806fc62d34034938ca2f29c783c94
出典データセット
uspto-grants-1993_09
特許番号
US05246915

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