Ethylene Glycol → HCID 67378455, compound

Participants

Reaction Steps

4-Cyanoacetophenone (5.0 g, 34.4 mmol) was dissolved in toluene (50 mL), had ethylene glycol (3.4 g, 55.1 mmol) and BF3 etherate (0.5 mL) added to it dropwise, was heated on a water separator for 12 h under reflux, allowed to cool to room temperature (yellow reaction solution), had a 5-percent sodium hydrogencarbonate solution (40 mL) added, was extracted with diethyl ether, washed with saturated sodium chloride solution (30 mL), dried over MgSO4, filtered, evaporated under vacuum, and recrystallized from diethyl ether/n-pentane (1:1), Yield: 2.2 g (34%) colorless solid, m.p. 70° C. 1H-NMR (200 MHz, CDCl3, 25° C.): δ=1.62 (s, 3 H, CH3), 3.72-3.75 (m, 2 H, CH2), 4.02-4.08 (m, 2 H, CH2), 7.57-7.64 ppm (m, 4 H, Haryl). HRMS (C11H12NO2): calc. m/z: 190.086, obs. m/z: 190.087, Δ=1 mmu.

Provenance & Evidence