4-Hydroxybiphenyl → Methyl 5-[(4-phenylphenoxy)methyl]furan-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

N,N-Dimethylformamide (400 mL) was added to sodium hydride (60% dispersion; ˜16 g, 0.4 mol) which had been washed with hexanes. The mixture was cooled to −5° C., and then a solution of 4-phenylphenol (73.12 g, 0.43 mmol) in N,N-dimethylformamide (150 mL) was added. The mixture was allowed to stir at room temperature for 2.5 h, and then a solution of 5-chloromethylfuran-2-carboxylic acid methyl ester (25 g, 0.14 mmol) in N,N-dimethylformamide (100 mL) was added. The reaction mixture was heated at ˜105° C. for 2 h, and then it was allowed to cool, evaporated under reduced pressure, and water was added. The mixture was extracted three times with ethyl acetate, and the combined organic layers were washed with saturated brine, dried (magnesium sulfate), filtered, evaporated, and purified using a Biotage 75 L purification system, eluting with 0-10% methylene chloride/toluene to give 5-(biphenyl-4-yloxymethyl)-furan-2-carboxylic acid methyl ester (20.5 g, 46%).

Provenance & Evidence