Sodium hydride → 3-(2,2-Dimethoxy-ethoxy)-4'-methoxy-4-methyl-biphenyl

Participants

Reaction Conditions

Reaction Steps

To NaH (357 mg (600 mg 60% in mineral oil, hexane washed 3×), 14.86 mmol) was added dry THF (100 ml), 4′-methoxy-4-methyl-biphenyl-3-ol (1.59 g, 7.43 mmol), and 2-bromo-1,1-dimethoxy ethane (1.76 g, 10.40 mmol). The reaction was stirred at 60° C. overnight, cooled, passed through a silica plug and concentrated to 1.66 g (74%) of product as a white solid: mp 3940° C.; 1H NMR (300 MHz, DMSO-d6): δ 2.17 (3H, s), 3.38 (6H, s), 3.79 (3H, s), 4.09 (2H, d, J=5.2 Hz), 4.73 (1H, t, J=5.2 Hz), 7.00 (2H, d, J=8.8 Hz), 7.09 (1H, dd, J=7.7 Hz, 1.5 Hz), 7.15 (1H, d, J=1.2 Hz), 7.18 (1H, d, J=7.8 Hz), 7.62 (2H, d, J=8.8 Hz); MS (ESI) m/z 303 ([M+H]+).

Provenance & Evidence