Hydrochloric Acid → 3-Hydroxybenzenepropanol

Participants

Reaction Steps

1.0M Lithium aluminum hydride in tetrahydrofuran (35.07 mL, 35.07 mmol) was added to a solution of 3-(3-hydroxyphenyl)propionic acid methyl ester (3.16 g, 17.5 mmol) in tetrahydrofuran (30 mL) at 0-5° C. under an argon atmosphere. The mixture was stirred at room temperature for 6 hours, and sodium sulfate decahydrate (15 g) was added to the mixture, followed by cooling to 0-5° C., and a dropwise addition of water (about 10 mL) and concentrated hydrochloric acid to pH 2-3. The mixture was extracted with ethyl acetate, and the extract was washed with water, brine, dried over magnesium sulfate, and concentrated to dryness. Purification by flash chromatography, eluting with hexane/ethyl acetate, gave 3-(3-hydroxypropyl)phenol as a clear oil (2.34 g, 88%).

Provenance & Evidence