Hydrochloric Acid → Methyl 3-hydroxy-4-iodobenzoate

Participants

Reaction Steps

A solution of methyl 4-amino-3-hydroxybenzoate (79 g, 0.47 mol), 3N HCl (750 mL), and THF (250 mL) was cooled to 0° C. A solution of NaNO2 (35.9 g, 0.52 mol) in 115 mL of water was added over ca. 5 minutes, and the solution was stirred for another 25 minutes. A solution of potassium iodide (312 g, 1.88 mol) in 235 mL of water was added all at once, and the reaction was stirred for an additional 15 minutes. The mixture was poured into EtOAc, shaken, and the layers were separated. The organic phase was washed with water and brine, dried (Na2SO4), and concentrated in vacuo to provide the crude product (148 g). Purification by column chromatography through silica gel (0%-50% EtOAc/hexane) provided the title compound. 1H NMR (CDCl3, 400 MHz): d 7.75 (d, 1H, J=8.2 Hz, ArH); 7.62 (d, 1H, J=2.0 Hz, ArH); 7.33 (dd, 1H, J=8.2 and 2.0 Hz, ArH); 5.56 (s, 1H, OH) and 3.91 (s, 3H, OCH3).

Provenance & Evidence