3-(3'-Hydroxyphenyl)propionic acid → Ethyl 3-(3-hydroxyphenyl)propanoate

Participants

Reaction Steps

A solution of 3-(3-hydroxyphenyl)propionic acid (Lancaster, 66.4 g, 0.4 mol) in ethanol (700 mL) was treated with concentrated sulfuric acid (6 mL), heated to reflux for 2 h, and allowed to cool to RT. The mixture was cooled in ice, neutralized with 10% aqueous sodium carbonate and concentrated in vacuo to about 50 mL. Water (˜200 mL) was added and the mixture was extracted three-times with ethyl acetate. The combined ethyl acetate extract was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo to yield the title compound as an oil (70 g, 90%).

Provenance & Evidence