Sodium Iodide → 10-Iododecanoic acid

Participants

Reaction Steps

To a mechanically stirred solution of 10-bromodecanoic acid (50 g, 0.2 mol) in 1 L of acetone under nitrogen was added sodium iodide (238.7 g, 1.59 mol) and the resulting heterogeneous reaction mixture was allowed to stir at room temperature for 18 h. The thick reaction mixture was filtered through a pad of Celite 521, concentrated in vacuo to one-fifth volume and diluted with 1 L of brine. This was extracted with 4×250 mL of hexanes. The combined organic extracts were washed with 2×250 mL of freshly prepared 10% aqueous sodium thiosulfate, dried over sodium sulfate, concentrated in vacuo and vacuum dried to give iodo acid 2 (57.5 g, 98%) as a white solid:

Provenance & Evidence