Dimethylformamide → 3-Isopropyl-4-methoxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-isopropylanisole (859 g, 5.85 mol) and POCl3 (2690 g, 17.5 mol) at 80° C. under N2, was slowly added DMF (1584 mL, 20.46 mol) at a rate such that the temperature remained between 80-90° C. After stirring for 16 hr at 85° C., the dark solution was poured cautiously onto 7 Kg of ice. (Quench required 1.5 hr due to violent exotherm) The mixture was extracted twice with EtOAc (total volume 16 L). The combined EtOAc layers were washed once with aq. NaHCO3 and then with brine. Upon concentration, 881 g of 4-formyl-2-isopropylanisole was obtained.

Provenance & Evidence