Ethanol → Ethyl 2-(4-bromophenyl)acetate

Participants

Reaction Steps

A solution of 63 grams (0.29 mole) of 4-bromophenyl acetic acid and 50 milliliters of concentrated sulfuric acid in 500 milliliters of absolute ethanol was refluxed for 8 hours then allowed to stand overnight. After pouring over 600 grams of ice, the mixture was extracted with ether/hexanes. The ether extracts were washed thoroughly with water and sodium bicarbonate solution then dried over anhydrous sodium sulfate. Removal of the solvent by rotary evaporation yielded 57 grams (0.24 mole, 80% isolated yield) of an oil which crystallized upon cooling. Filtration and washing with hexane afforded pure product.

Provenance & Evidence