Toluene → 2-Amino-3-[4-(1,1-dimethylethyl)phenoxy]propanol

HRID 35934노트

반응식

HRID 35934 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][CH:8]([CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=1)[C:9](O)=[O:10].C1(C)C=CC=CC=1.[OH-].[Na+]>O1CCCC1.O>[NH2:7][CH:8]([CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:18][CH:19]=1)[CH2:9][OH:10]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 194240672-Amino-3-[4-(1,1-dimethylethyl)phenoxy]propionic acidHCID 21226445Aluminium lithium hydride

생성물 1

HCID 152799222-Amino-3-[4-(1,1-dimethylethyl)phenoxy]propanol수율 89.6%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a mixture of 4.00 g (105 mmol.) of lithium aluminum hydride and 50 ml of anhydrous tetrahydrofuran, there was added dropwise a solution of 2.50 g (10.5 mmol.) of 2-amino-3-[4-(1,1-dimethylethyl)phenoxy]propionic acid obtained in Production Example 13 in 50 ml of anhydrous tetrahydrofuran with stirring under reflux by heating for 30 minutes. Then the reaction mixture was further refluxed by heating with stirring for 2 hours. After the reaction was completed, the resultant mixture was cooled to a temperature of from 5° C. to 10° C. To the resultant mixture, there was added 100 ml of toluene and further added slowly, 10 ml of water and a 5N aqueous solution of sodium hydroxide. The above mixture was dried over anhydrous magnesium sulfate, filtrated with a filter agent (Celite®) and concentrated under reduced pressure to give 2.10 g of 2-amino-3-[4-(1,1-dimethylethyl)phenoxy]propanol as a light-yellowish solid (m.p. 101.7° C.).

후처리

  1. temperatureunder reflux
  2. temperatureby heating for 30 minutes
  3. temperatureThen the reaction mixture was further refluxed
  4. temperatureby heating
  5. stirringwith stirring for 2 hours
  6. additionfurther added slowly
  7. dry with materialThe above mixture was dried over anhydrous magnesium sulfate
  8. filtrationfiltrated with a filter agent (Celite®)
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5d1be88494ec45409b357ec324562b9b
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05411979

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