Water → p-Methylphenethylamine

HRID 280325

Reaction equation

HRID 280325 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH2:8])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 76280p-TolylacetonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 76751p-MethylphenethylamineYield 112.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

4-Methylbenzyl cyanide (10 g) in ether was added dropwise under nitrogen to lithium aluminium hydride (2.9 g) in ether. The solution was refluxed for 1 h at the end of addition. The reaction mixture was cooled, water (3 ml), 2N.NaOH (3 ml), and further water (9 ml) were added, the reaction mixture filtered, the residue washed with chloroform and the combined solvents dried (MgSO4). Evaporation gave 2-(4-methylphenyl)ethanamine (11.59 g).

Workup

  1. temperatureThe solution was refluxed for 1 h at the end of addition
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe reaction mixture filtered
  4. washthe residue washed with chloroform
  5. dry with materialthe combined solvents dried (MgSO4)
  6. customEvaporation

Sources & evidence

ORD record
ord-8d346d46b6794136a0e86b9fa123deeb
Source dataset
uspto-grants-1986_05
Patent number
US04588749

Linked notes

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