Toluene → HCID 68888626, compound

Participants

Reaction Steps

A mixture of 7.6 g (E)/(Z)-2-[(3-fluoro-2-methyl-phenyl)-hydrazono]-propionic acid ethyl ester and 8.2 g p-toluenesulfonic acid (dried by azeotropic distillation with toluene) was heated 1 h at reflux in toluene. The solution was cooled, poured into half-saturated aqueous sodium bicarbonate solution, and the aqueous phase extracted twice with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and evaporated. The residue was purified by column chromatography on silica gel (8:1 to 6:1 hexane/ethyl acetate eluant) to afford the title compound as a light brown solid, (24% yield, mp 149° C.; EI-MS m/e: 221.1 (M+))

Provenance & Evidence