Hydrochloric Acid → Ethyl 7-(4-hydroxyphenyl)heptanoate

Participants

Reaction Steps

A 500 ml single-neck flask was charged with 7-(4-hydroxyphenyl)heptanoic acid (A4) (17.7 g, 79.7 mmole), 35 ml of the 25% HCl solution, and ethanol (90 ml). The flask was immersed in an oil bath and refluxed 4.5 hours. After cooling to room temperature, the contents were poured onto ice water (750 ml) and 375 ml of saturated sodium bicarbonate were added. The mixture was extracted with ether (3×225 ml), the combined organic layers dried (MgSO4), and concentrated by rotary evaporation (2-4 hours at 45° C.). The resulting oil, Ethyl 7-(4-hydroxyphenyl)heptanoate, was of sufficient purity to be used in the next step.

Provenance & Evidence