Formaldehyde → HCID 14652260, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of paraformaldehyde (7.14 g, 238 mmol), diethylamine (27.6 ml, 260 mmol) and cupric acetate monohydrate (1 g) in dioxane (40 ml) was heated in an oil bath of 60° C. for 1 hour. When the solid material disappeared, pent-4-yn-1-ol (20 g, 238 mmol) was added and the heating at 95° C. was continued until the greenish suspension had been completely replaced by the thin brown precipitate (approximately 3 hours). After cooling to 20° C., the reaction mixture was poured into 10% aqueous KOH (40 ml). The precipitate was filtered off and washed with ether (100 ml). The organic phase was washed with water (5 times 50 ml), dried (K2CO3) and evaporated to dryness to give crude product. The isolated product was distilled to yield 29.78 g (74%) of 6-diethylaminohex-4-yn-1-ol: bp 92°-94° C. (0.1 mm Hg), IR (neat) 3309 cm-1 ; 1H NMR (CDCl3) δ4.1(S, 1H), 3.6(t, 2H), 3.3(m, 2H), 2.7-2.0(m, 6H), 2.0-1.4(m, 2H), 1.0(t, 6H).

Provenance & Evidence