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

HRID 743089Notes

Reaction equation

HRID 743089 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-b9646c4a03ef426caf642cdd61bb98b9
Source dataset
uspto-grants-1996_09
Patent number
US05556867

Reaction notes

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