Nitrogen → 12-(m-Iodophenyl)dodecyl methane sulfonate

Participants

Reaction Steps

12-m-Iodophenyldodecanol (5.88 g, 15.17 mmol) was placed into a flame-dried three-neck 100 ml round-bottomed flask equipped with a reflux condenser and charged with N2. Anhydrous pyridine (30 ml) was added. The mixture was cooled to 0° C. before freshly distilled methanesulfonyl chloride (2.0 ml, 25.96 mmol) was added drop-wise. The reaction mixture was allowed to warm to room temperature. After the reaction mixture had been stirred for several hours, it was poured into ice cold H2O and the resulting precipitate was filtered. The solid was dissolved in ether and extracted with H2O, 1N HCl, and H2O. The ether layer was dried (MgSO4) and the solvent was evaporated in vacuo. The crude product was recyrstallized with a hexanes and ethyl acetate mixture to yield the pure mesylate, compound 9, 12-(m-iodophenyl)dodecyl methane sulfonate (4.95 g, 70.7%).

Provenance & Evidence