Ethanol → Ethyl 4-iodobenzoate

Participants

Reaction Steps

A mixture of 21.0 g of 4-iodobenzoic acid, 100 ml of absolute EtOH and 6 ml of concentrated sulfuric acid was refluxed with stirring for 6 days. At the end of this time the reaction mixture was concentrated by boiling and an additional 4 ml of concentrated sulfuric acid added. The mixture was then refluxed for an additional 11 days, after which the mixture was cooled and 50 g of ice and 150 ml Et2O were added. The phases were separated and the aqueous layer was extracted with Et2O. The combined organic phases were washed with water, sat. aqueous NaHCO3 and water. The organic phase was then dried over MgSO4 and concentrated under vacuum to provide the title compound as a clear brownish liquid.

Provenance & Evidence