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

Participants

Reaction Steps

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.

Provenance & Evidence