Beta-Alanine → HCID 22753443, compound

Participants

Reaction Steps

A mixture of 1.00 g (2.17 mmol) of bis(3,5-di-tert-butyl-4-hydroxyphenyl)cyclopropenone 4, 0.29 g (4.3 mmol) of malonitrile and 0.02 g of β-alanine in 3.0 ml of freshly distilled acetic anhydride was heated to reflux with stirring for 20 min. A white precipitate formed in the reddish brown solution. The mixture was cooled to room temperature, and the precipitate was collected by filtration and recrystallized from benzene to give 0.62 g (56%) of 6a as pale yellow needles; mp 280-281°, (dec); ir (KBr) 3560(m), 2960-2860(m), 2213(m), 2197(m), 1850(w), 1595(m), 1490(s), 1470(m), 1450(w), 1410(s), 1370(s), 1360(s), 1310(s), 1255(s), 1240(m), 1200(w), 1100(m), 1025(w), 925(w), 900(w), 890(sh), 885(w), 780(w), 760(w), 675(2), 655(w), 595 cm-1 (w); nmr (CDCl3) δ1.52(s, 36HO), 5.98(s,2H), 7.91(s,4H); uv-visible λmax (methanol) 233 nm (log 4.40), 242(4.34), 252(4.29), 299(4.62), 313(4.57), 368(4.54), 396(sh) (4.44); only the longest wavelength absorptions will be shown for the uv-visible spectrum in nonpolar solvents, λmax (benzene) 381 nm, 400(sh); mass spectrum m/e 510.32500 (calc. 510.32462); Anal. Calcd. for C34H42N2O2 : C, 79.95; H, 8.29; N, 5.49. Found: C, 80.03; H, 8.32; N, 5.43.

Provenance & Evidence