Water → Decane

Participants

Reaction Steps

Reduction of undecanenitrile in n-propylamine, ethylenediamine, and t-butanol. Lithium, (0.28 g, 40 mmol) in small pieces, was added to undecanenitrile (0.775 g, 4.63 mmol) in n-propylamine (10 mL), ethylenediamine (1.5 g, 25 mmol) and t-butanol (2.22 g, 30 mmol). After 20 min, the temperature increased to 55° and decreased slowly. After another 2 hr, the reaction mixture was poured onto a slurry of water (25 mL) and ice (25 g). The reaction mixture was extracted twice with ether (25 mL and 50 mL). The ether extract was analyzed by glpc using ethyl benzoate as internal standard. Glpc analysis showed n-decane in 17% yield and undecylamine in 83% yield. A similiar reaction using methanol in place of t-butanol in the same mole ratio gave the same percentages of n-decane and undecaneamine.

Provenance & Evidence