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

HRID 743089ノート

反応式

HRID 743089 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-b9646c4a03ef426caf642cdd61bb98b9
出典データセット
uspto-grants-1996_09
特許番号
US05556867

反応ノート

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