Water → 2-(3,4-dimethylphenoxy)ethanamine

HRID 1741437Notes

Reaction equation

HRID 1741437 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH3:13])[O:5][CH2:6][C:7]([NH2:9])=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>O1CCCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH3:13])[O:5][CH2:6][CH2:7][NH2:9]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 4931447HCID 4931447, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 19914222-(3,4-dimethylphenoxy)ethanamineYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.50 g (13.9 mmol) of (3,4-dimethylphenoxy)acetamide obtained in step 3 was dissolved in 50 ml of dry tetrahydrofuran, and added slowly to a solution of 1.05 g (27.8 mmol) of LiAlH4 in 70 ml of dry tetrahydrofuran. The reaction mixture was refluxed for 5 hours and then 5 ml of water and 5 ml of 1N sodium hydroxide were added to decompose the remaining LiAlH4. The resultant mixture was passed through a Celite™ layer and the filtrate was evaporated under a reduced pressure to produce a residue, which was distilled under a reduced pressure to obtain 0.63 g (yield 28%) of the title compound as a colorless oil.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. customthe filtrate was evaporated under a reduced pressure
  3. customto produce a residue, which
  4. distillationwas distilled under a reduced pressure

Sources & evidence

ORD record
ord-c122dbe3ea4e4c77afabbc2d5f47197b
Source dataset
uspto-grants-1999_10
Patent number
US05973201

Reaction notes

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