Dimethyl Sulfoxide → 4-(4-Benzyloxyphenyl)phenol

Participants

Reaction Steps

The process started with the synthesis of 4′-benzyloxybiphenyl-4-ol potassium salt. This compound was synthesized similar to the literature procedure for its preparation (Hay, A. S., Williams, H. M., Relles, Boulette, B. M., Donahue, P. B., Johnson, D. S. J. Polym. Sci. Polym. Lett. Ed. 1983, 21, 449; Hay, A. S., Williams, P. J., Relles, H. M., Boulette, B. M. J. Macromol. Sci-Chem. 1984, A21, 1065). A mixture of 4,4′-dihydroxybiphenyl (27.6 g, 100. mmol), 50% aqueous sodium hydroxide (8.00 g, 100. mmol in 16.0 mL water), 100 mL of DMSO and 100 mL of toluene was heated at reflux with a Dean Stark trap until all visible traces of water had been removed. The toluene was distilled from the system to give a homogeneous solution of 4′-benzyloxy-biphenyl-4-ol in DMSO for the next reaction. The yield was considered quantitative. 1H NMR (DMSO-d6): δ 5.08 (2H, s, >CH2), 6.70 (2H, d), 6.98 (2H, d), 7.29–7.44(9H. m). IR (neat, cm−1): 3036, 2866, 2577, 2340, 1734, 1610, 1501, 1377, 1247, 1177, 1106, 1027, 1000, 815, 747, 700.

Provenance & Evidence