Ethylenediamine → Decanal

Participants

Reaction Steps

n-Propylamine solution with t-butanol. A solution of N-benzyl-N-methyldecanoic acid amide (10 g, 0.036 mol) in n-propylamine (100 mL), ethylenediamine (13 g, 0.216 mol) and t-butanol (16 g, 0.216 mol) was cooled to -18° and lithium (1.77 g, 0.252 mol), in small pieces, was added rapidly. After 15 min, the temperature raised to 12° and then lowered. After another 45 min, the reaction turned blue and after another 30 min a yellow solution was obtained. The reaction mixture was poured over 75 g of crushed ice and water (75 mL). The mixture was extracted with ether (2×75 mL) and the combined ether extracts were washed with brine (2×50 mL). The ether was evaporated and the residue was dissolved in THF (50 mL) and 3N hydrochloric acid (15 mL). The solution was heated under reflux for 2 hr and then cooled and diluted with brine (50 mL). The mixture was extracted with ether (2×75 mL) and the combined ether extracts were washed with brine (1×50 mL) and filtered through 1PS filter paper. The ether was evaporated and the residue was distilled to give 2.0 g (36%) of n-decanal having a bp 100°-105° (15 mm).

Provenance & Evidence