Hydrochloric Acid → 2-Iodo-3-methoxybenzoic acid

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 3-methoxy-2-pivalamidobenzoic acid (20 g, 0.08 mol) and 7M hydrochloric acid (280 ml) was heated under reflux for 2 hours then cooled to 0° C. A solution of sodium nitrite (5.8 g, 0.09 mol) in water (46 ml) was added dropwise at <5° C., the mixture was stirred at 0-5° C. for 2 hours, then a solution of potassium iodide (17.8 g, 0.11 mol) in water (39 ml) was added dropwise at 0-5° C. The stirred mixture was heated at 70-80° C. for 2 hours then cooled in ice. The product was extracted into ethyl acetate (3×300 ml), the combined extracts were washed with 20% aqueous sodium thiosulphate solution (3×300 ml), then they were dried (MgSO4) and the solvent was removed in vacuo to leave 2-iodo-3-methoxybenzoic acid (13 g, 58%) as a solid, m.pt. 142-146° C.

Provenance & Evidence