Hydrochloric Acid → 4-iodo-2-methoxyphenol

Participants

Reaction Conditions

Reaction Steps

4-Iodo-2-methoxyphenol was prepared according to the method described by K. J. Edgar and N. Falling, J. Org. Chem. 55, 5287 (1990). Guaiacol (50.0 g, 402 mmol), sodium iodide (60.5 g, 402 mmol) was dissolved in methanol (800 ml) and cooled to 0° C., and sodium hydroxide (16.0 g, 402 mmol) was added at such a rate that the temperature did not exceed 5° C. An aqueous solution of sodium hypochlorite (750 ml, 7.2% solution, 402 mmol) was added during 45 min. The temperature was not allowed to exceed 0° C. After completed addition it was stirred for another 10 minutes at 0° C. First aqueous hydrochloric acid (100 ml, 4 M solution) and then sodium sulfite (200 ml saturated aqueous solution) was added. The product was extracted with ether was followed by drying over magnesium sulfate. Evaporation of the solvent was followed by distillation and the fraction at 105-106° C. at 0.1 mm Hg was collected. Yield 55 g, 54%.

Provenance & Evidence