Ammonia → 2-(3,5-Dimethyl-phenoxy)-1-methyl-ethylamine

HRID 1975536

反応式

HRID 1975536 の反応式
[CH3:1][CH:2](O)[CH2:3][O:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[CH:6]=1.[NH3:14].[H][H]>[Cr].[Cu]>[CH3:12][C:7]1[CH:6]=[C:5]([CH:10]=[C:9]([CH3:11])[CH:8]=1)[O:4][CH2:3][CH:2]([NH2:14])[CH3:1]

参加物

5

反応物 3

HCID 222Ammonia2 回HCID 110739942-Propanol, 1-(3,5-dimethylphenoxy)-HCID 178418361HCID 178418361、化合物

生成物 1

HCID 53052572-(3,5-Dimethyl-phenoxy)-1-methyl-ethylamine収率 43.1%

試薬・触媒・溶媒 1

HCID 9833946Chromium, compd. with copper (1:1)触媒

実験手順

A 150 cc autoclave was charged with 50.0 g (277 mmol) of 1-methyl-2-(3,5-dimethylphenoxy)ethanol, 15.4 g of a copper-chromium catalyst (N202, supplied by Nikki Chemical Co.: CuO 44-46%, Cr2O3 43-44%, MnO2 4-5%) preliminarily activated under a hydrogen current at 200° to 300° C. for 3 hours and 7.5 g (440 mmol) of ammonia, and the resultant mixture was stirred under a hydrogen pressure of 40 kg/cm2G at 250° C. for 2 hours. After the reaction mixture was allowed to cool, the pressure of excess ammonia and hydrogen was released, and the catalyst was removed by filtration. And, 200 ml of ethyl ether was added to the filtrate, and the mixture was subjected to extraction with 200 ml of a 20% hydrochloric acid aqueous solution. The extracted water layer was rendered alkaline with a 20% sodium hydroxide aqueous solution, and it was subjected to extraction with 200 ml of ethyl ether. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to give 21.4 g of 1-(3,5-dimethylphenoxy)-2-aminopropane (yield 43%). This yield is higher than that which could be attained by the conventional method described in JP-A-63-264465. The starting 1-methyl-2-(3,5-dimethylphenoxy)ethanol in an amount of 23.9 g (48%) was recovered from the organic layer extracted with the hydrochloric acid aqueous solution. The selectivity of the intended product, calculated on the basis of the amount obtained by deducting an unreacted starting material from the total amount of the starting material, was 82%. This selectivity was also higher than that which could be attained by the conventional method described in Polish Laid-open Patent Publication No. 142,711.

後処理

  1. temperatureto cool
  2. customthe catalyst was removed by filtration
  3. additionAnd, 200 ml of ethyl ether was added to the filtrate
  4. extractionthe mixture was subjected to extraction with 200 ml of a 20% hydrochloric acid aqueous solution
  5. extractionwas subjected to extraction with 200 ml of ethyl ether
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-44ba819ffb1143b58ef9e54b099f1578
出典データセット
uspto-grants-1994_02
特許番号
US05286905

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