Hydrogen iodide → HCID 20513474, compound

Participants

Reaction Steps

A mixture of ethyl 2-cyano-2-[2-methoxy-3-(o-tolyloxy)phenyl]-n-nonanoate (6.7 g), hydriodic acid (58%, 10 ml) and acetic acid (30 ml) was refluxed under heating for 45 hours. The reaction mixture was concentrated under reduced pressure, and the residue was poured into water and extracted with diethyl ether. The extract was washed with aqueous sodium hydrogen sulfite and water in turn, dried and evaporated under reduced pressure. To the residue were added potassium hydroxide (5 g) and methanol (30 ml), and the mixture was refluxed under heating for an hour. After evaporation, the residue was dissolved in water, and the aqueous solution was washed with diethyl ether, acidified with conc. hydrochloric acid and then extracted with diethyl ether. The extract was washed with water, dried and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 90 g, benzene-ethyl acetate 1:1) to give 2-[2-hydroxy-3-(o-tolyloxy)phenyl]-n-nonanoic acid (4.3 g).

Provenance & Evidence