Hydrochloric Acid → 3-{[4-(Difluoromethoxy)phenyl]ethynyl}benzaldehyde

Participants

Reaction Steps

Into a mixture of 2-(3-{[4-(difluoromethoxy)phenyl]ethynyl}phenyl)-1,3-dioxolane, (1.0 g, 3.1 mmol) and THF (5 mL) was added HCl (2N, 1 mL). The mixture was stirred at room temperature for 2 hours, poured into water and extracted with EtOAc/ethyl ether 1/1. The organic extracts were dried over MgSO4. Evaporation and purification on silica gel (ISCO) using hexanes/EtOAc (3/1) as the eluting solvents gave 3-{[4-(difluoromethoxy)phenyl]ethynyl}benzaldehyde as a yellow oil (3.65 g, 95% yield), MS m/e M+ 272; 1H NMR (400 MHz, DMSO-d6) 3.9-4.05 (m, 4H), 5.72 (s, 1H), 7.1-7.3 (m, 4H), 7.62 (m, 2H), 7.8-7.9 (m, 2H), 8.03 (s, 1H), 9.99 (s, 1H).

Provenance & Evidence