Methyl 4-(4-hydroxymethylphenyl)benzoate

Synthesis

To 4-bromobenzyl alcohol (500 mg, 2.94 mmol) and 4-methoxycarbonylphenylboronic acid (550 mg, 3.53 mmol) were added Pd(OAc)2 (200 mg, 735 μmol) and Na2CO3 (3 g, dissolved in 20 mL of H2O) as a raw material after dissolution in DMF (20 mL). The reaction mixture was stirred at 70 °C for 48 hours. After completion of the reaction, extraction was carried out with EtOAc, the organic layers were combined and washed with brine, dried over MgSO4, filtered and concentrated in vacuum. Purification by column chromatography (eluent: EtOAc/n-heptane, 1:4) afforded the target product methyl 4'-(hydroxymethyl)-[1,1'-biphenyl]-4-carboxylate (170 mg, 24% yield) as white crystals. rf = 0.3 (EtOAc/n-heptane, 1:1). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 8.15-8.06 (m, 2H), 7.70-7.58 (m, 4H), 7.52-7.43 (m, 2H), 4.77 (d, J = 3.1 Hz, 2H), 4.07-3.67 (m, 3H), 1.75 (br s, 1H, OH) ppm. FTIR spectra showed characteristic absorption peaks: 3305, 3032, 1718, 1604, 1432, 1399, 1286, 1271, 1220, 1117, 765 cm-1. HRMS (EI) analysis results: calculated value C15H14O3 (M)+ 242.0942, measured value 242.0919.

References

[1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 20, p. 5593 - 5603