Ethyl 4-cyano-3,5-dimethylbenzoate → [4-(Aminomethyl)-3,5-dimethylphenyl]methanol

HRID 1282062Notes

Reaction equation

HRID 1282062 reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].[C:7]([C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16](OCC)=[O:17])=[CH:11][C:10]=1[CH3:21])#[N:8]>O1CCCC1.O>[NH2:8][CH2:7][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH2:16][OH:17])=[CH:11][C:10]=1[CH3:21]

Participants

5

Reactant 2

HCID 18423069Ethyl 4-cyano-3,5-dimethylbenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 23383595[4-(Aminomethyl)-3,5-dimethylphenyl]methanolYield 233.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of aluminum lithium hydride (2.1 g) in tetrahydrofuran (20 ml) was added a solution of ethyl 4-cyanomesitylenate (2.9 g) in tetrahydrofuran (30 ml) at 0° C. and the mixture was refluxed under heating for 6 hr. To this reaction mixture was added 50% (v/v) tetrahydrofuran in water under ice-cooling. This mixture was stirred at room temperature for 30 min and the catalyst was filtered off using Celite. The solvent was evaporated and the obtained residue was recrystallized from methanol-isopropyl ether to give the title compound (5.5 g) as white crystals.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 6 hr
  3. temperaturecooling
  4. filtrationthe catalyst was filtered off
  5. customThe solvent was evaporated
  6. customthe obtained residue was recrystallized from methanol-isopropyl ether

Sources & evidence

ORD record
ord-51485f7b3b6e48b28190ac4524c7d045
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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