Sulfuric Acid → Propan-2-yl 2-hydroxy-5-iodobenzoate

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Reaction Steps

2-Hydroxy-5-iodobenzoic acid (I 84 g, 0.7 mol), isopropanol (50 ml), conc sulfuric acid (5 ml) and p-toluenesulfonic acid (10 g) in toluene (1 1) was refluxed using a water separator. Portions of isopropanol was added intermittently to compensate for loss of 2-propanol by dehydration. After 24 h, the solution was cooled and washed with water. The toluene was evaporated partially. Iso-octane was added, and precipitated 2-hydroxy-5-iodobenzoic acid (106 g) filtered off. The solution was taken to dryness and the residue recrystallized from methanol. Yield 64 g, (71%), corrected for recovered starting material).

Provenance & Evidence