Hydrochloric Acid → 3-(4-Hydroxyphenyl)hex-4-ynoic acid

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Reaction Steps

A solution of 5-[1-(4-hydroxyphenyl)but-2-ynyl]-2,2-dimethyl-1,3-dioxane-4,6-dione (20 g, 69.44 mmol) in pyridine-water (5:1, 390 mL) is heated at reflux for 16 hours and after cooling is acidified to pH ˜2 with 5 N HCl and extracted with EtOAc (2×300 mL). The combined extracts are washed with saturated brine, dried over MgSO4, filtered, and concentrated to give an off-white solid (13.5 g, 96%). ESI/MS m/z 203 (M−H)−.

Provenance & Evidence