Acetic Acid → Methyl 4-Formylbenzoate

Participants

Reaction Steps

A mixture of 68.7 g (0.3 mole) of methyl-α-bromotoluate, 84 g (0.6 mole) of hexamethylenetetraamine, 150 ml of acetic acid and 150 ml of water were refluxed with stirring for two hr. Ninety ml of concentrated hydrochloric acid was then added and kept at room temperature for 15 min. The cooled solution was extracted with ether, washed with water, 10% NaHCO3 solution, water and dried. Evaporation of the solvent and recrystallization of the residue from petroleum ether gave 35 g of p-carbomethoxybenzaldehyde, yield 71% m.p. 61°-63° C. (lit. m.p. 61°-63° C.). The infrared spectrum showed absorption at 1720 cm-1 ##STR6## 1690 cm-1 (--CHO). NMR (CDCl3) δ3.8 (s,--COOCH3,3), 7.8-8.2 (m, aromatic, 4), and 10.2 (s,--CHO,1)

Provenance & Evidence