12-(3-Iodophenyl)dodecanoic acid → 12-m-Iodophenyldodecanol

Participants

Reaction Steps

Anhydrous THF (20 ml) was added to a flame-dried 100 ml two-necked flask containing 12-m-iodophenyldodecanoic acid (3.30 g, 8.21 mmol). The solution was cooled in an ice bath before BH3 -THF (15.0 ml, 1M) was added dropwise. The reaction mixture was allowed to warm to room temperature and to stir under anhydrous conditions for 20 hours. The reaction mixture was again cooled to 0° C. and quenched with H2O. Ether and additional H2O were then added. The ether layer was extracted with H2O, sat. NaHCO3, and more H2O and dried (MgSO4). The solvent was removed under reduced pressure to yield a yellow oil. The crude compound was purified by column chromatography (90 g silica gel, hexanes:ethyl acetate 8:1) to yield a white solid, compound 8, 12-m-iodophenyldodecanol (3.14 g, 98.4% yield).

Provenance & Evidence