Hydrochloric Acid → Ethyl-12-(m-iodophenyl)-dodecanoate

Participants

Reaction Steps

Glacial acetic acid (4 ml) and concentrated HCl (2.5 ml) were added to a 50 ml Erlenmeyer flask containing ethyl-12-(m-aminophenyl)-dodecanoate (3.92 g, 12.28 mmol). The mixture was cooled in a NaCl/ice bath. A cold aqueous solution of NaNO2 (4 ml, 3.1M) was added to the mixture. The reaction was stirred for 40 minutes before a cold aqueous solution of KI/I2 (2.31/1.78 g, 7 ml) was added. The reaction mixture was allowed to warm to room temperature and was stirred overnight. Ether was added to the reaction mixture. The ether layer was separated and extracted with H2O, 10% Na2S2O3, H2O, sat. NaHCO3, and brine. The organic layer was dried (MgSO4) and the solvent removed under reduced pressure to give a reddish oil. The crude product was purified by column chromatography (120 g silica gel, hexanes:ethyl acetate 20:1) to yield a clear oil, compound 6, ethyl-12-(m-iodophenyl)-dodecanoate (5.28 g, 56.8% yield).

Provenance & Evidence