Phenol → 2,2-Bis(4-hydroxyphenyl)propanoic acid

Participants

Reaction Steps

To a cooled mixture of phenol (9.4 g, 0.1 mol), pyruvic acid (4.4 g, 0.05 mol), and water was added concentrated H2SO4 (4.5 mL, 18.0 g) dropwise with stirring. After 15 minutes the ice bath was removed and the reaction was warmed to room temperature and stirred for 18 hours. The reaction mixture was diluted with ethyl ether/water (200 ml 1:1) and the layers were separated. The organic layer was extracted with saturated aqueous NaHCO3. The aqueous extract was then acidified, extracted with ethyl ether, dried over MgSO4, filtered, and concentrated in vacuo to give 2,2-bis(4-hydroxyphenyl)propionic acid (6.2 g) as a colorless sticky oil.

Provenance & Evidence