3-(Dimethylamino)phenol → 3-Dimethylaminophenyloctyl ether

HRID 129898

反応式

HRID 129898 の反応式
[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[C:5](O)[CH:6]=[CH:7][CH:8]=1.[OH-:11].[Na+].[CH2:13](Br)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[C:5]([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][O:11][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([N:2]([CH3:10])[CH3:1])[CH:4]=2)[CH:6]=[CH:7][CH:8]=1

参加物

6

反応物 3

HCID 74213-(Dimethylamino)phenolHCID 81401-BromooctaneHCID 14798Sodium Hydroxide

生成物 1

HCID 541676423-Dimethylaminophenyloctyl ether

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

200 ml of toluene, 54.8 g (0.4 mol) of 3-dimethylaminophenol and 13.58 g (0.04 mol) of tetrabutylammonium hydrogen sulfate are placed in a 750 ml sulfonating flask having an anchor mixer, thermometer, reflux condenser and dropping funnel and at RT 80 g (1.0 mol) of a 50% aqueous NaOH solution are added dropwise in the course of 30 minutes. The suspension is then stirred for 30 minutes at 80° C. and then at the same temperature 154 g (0.8 mol) of octyl bromide are added in the course 45 minutes. After a subsequent reaction period of 2.5 hours the mixture is cooled and filtered, and the filtrate is washed with 1×70 ml of H2O, dried over MgSO4, filtered and concentrated by evaporation. The crude product is distilled under a high vacuum, yielding 65.5 g of 3-dimethylaminophenyloctyl ether in the form of a colourless liquid having a boiling point of 150°-152 ° C. (0.1 mbar) which no longer has an OH band in the IR spectrum and of which the NMR analysis is in agreement with the sand structure.

後処理

  1. temperaturethermometer, reflux condenser
  2. customAfter a subsequent reaction period of 2.5 hours the mixture
  3. temperatureis cooled
  4. filtrationfiltered
  5. washthe filtrate is washed with 1×70 ml of H2O
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation
  9. distillationThe crude product is distilled under a high vacuum

出典と根拠

ORDレコード
ord-dc2799b643e844368c9d3d4553261905
出典データセット
uspto-grants-1995_11
特許番号
US05470896

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