Reaction #531786

Reaction equation

water

4-aminobenzyl cyanide

pyridine

chloride

→

desired product

N-(4-cyanomethylphenyl) p-menthanecarboxamide

Conditions

Workup

1. 1
   OtherThe mixture was separated
2. 2
   WashThe organic layer was washed with 50 mL of water and 50 mL of brine
3. 3
   DryingThe organic layer was dried over MgSO4
4. 4
   OtherThe solvent was evaporated in vacuo
5. 5
   Otherto afford the crude product, which
6. 6
   Otherwas recrystallized from hexanes

Procedure

To a flask, were added 6.6 g (50 mmol) of 4-aminobenzyl cyanide, 4.04 mL of pyridine and 100 mL MtBE. To this mixture, 10 g of p-menthane-3-carbon*yl chloride were added dropwise over 5 minutes. The reaction mixture was stirred for 24 h. To the reaction mixture, 50 mL of water were added. The mixture was separated. The organic layer was washed with 50 mL of water and 50 mL of brine. The organic layer was dried over MgSO4. The solvent was evaporated in vacuo to afford the crude product, which was recrystallized from hexanes to afford 10.1 g of the desired product with the following spectroscopic properties:

Source