Hydrochloric Acid → 2-(4-Iodophenoxy)ethanol

Participants

Reaction Conditions

Reaction Steps

A melt of ethylene carbonate (6.5 g, 74 mmol) in a small flask under Argon was treated with 4-iodophenol (0.400 g, 1.82 mmol) and powdered potassium carbonate (1.26 g, 9.1 mmol) and was stirred at 90° C. for 3 hr. The mixture was treated with cold dilute hydrochloric acid to decompose the excess potassium carbonate and excess aqueous sodium hydroxide solution was slowly added and the mixture was stirred over night. The suspension was extracted with methylene chloride, was washed with water and brine, was dried over sodium sulfate and was stripped to afford a white solid, which was purified by flash chromatography on silica gel (20 mL) with methylene chloride to afford (0.128 g, 27%) of the titled intermediate as a white solid, mp 76°-77.5° C.

Provenance & Evidence