3-(Dimethylamino)phenol → 3-Dimethylaminophenylbutyl ether

HRID 129897

反応式

HRID 129897 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][CH3:16]>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]([CH2:16][CH2:15][CH2:14][CH2:13][O:11][CH2:4][CH2:3][CH2:8][CH2:7][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 8002Butyl bromideHCID 14798Sodium Hydroxide

生成物 1

HCID 538101413-Dimethylaminophenylbutyl 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

54.8 g (0.4 mol) of 3-dimethylaminophenol and 13.58 g (0.04 mol) of tetrabutylammonium hydrogen sulfate are placed in 200 ml of toluene 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 109.6 g (0.8 mol) of butyl bromide are added in the course of 45 minutes. After a subsequent reaction period of 2 hours the mixture is cooled and filtered, and the filtrate is washed once with 70 ml of H2O, dried over MgSO4, filtered and concentrated by evaporation. The crude product is distilled under a high vacuum, yielding 64 g of 3-dimethylaminophenylbutyl ether in the form of a colourless liquid having a boiling point of 94° -96° C. (0.08 mbar) which no longer has an OH band in the IR spectrum and of which the NMR analysis is in agreement with the said structure.

後処理

  1. temperaturethermometer, reflux condenser
  2. customAfter a subsequent reaction period of 2 hours the mixture
  3. temperatureis cooled
  4. filtrationfiltered
  5. washthe filtrate is washed once with 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-bc8900e9dc9e4d808a9a8c7fb114b8b5
出典データセット
uspto-grants-1995_11
特許番号
US05470896

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