4-Hydroxybiphenyl → HCID 6496944, compound

Participants

Reaction Steps

ExxonMobil™ Aromatic 100 solvent (300 mL) was added into a 3-neck round bottom flask containing 4-phenylphenol (50.00 g, 294 mmol) and stirred for 15 minutes at room temperature. Potassium hydroxide pellets (1.9 g, 293 mmol) were added and the mixture heated to reflux temperature for 10 minutes. 2-oxazolidinone (26.5 g, 294 mmol) was added, and the reaction mixture continued to stir at reflux temperature for 4 hours. Additional 2-oxazolidinone (8.05 g, 92.4 mmol) was added and the reaction mixture was allowed to continue stirring at reflux for an additional 4 hours. After indication of complete conversion of 4-phenylphenol by TLC, the reaction mixture was allowed to cool to room temperature. The crude reaction mixture was filtered and the filtrate was collected. The solvent was evaporated in vacuo to obtain 14.5 g (23%) of the amine as a white solid. 1H NMR (DMSO, 400 MHz) δ 7.63-7.55 (m, 4H), 7.45-7.40 (m, 2H), 7.34-7.28 (m, 1H), 7.05-7.00 (m, 2H), 3.95 (dd, 2H, J=5.8, 5.8 Hz), 2.89 (dd, 2H, J=5.8, 5.8 Hz). 13C NMR (DMSO, 400 MHz) δ 158.3, 139.8, 132.4, 128.8, 127.7, 126.6, 126.1, 1 f4.9, 70.3, 41.0. MS (ESI) for C14H15NO [M+H] calc. 213.28. found 213.96.

Provenance & Evidence