O-Cresol → 4-[1-(4-Bromophenyl)-1-ethylpropyl]-2-methylphenol

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 3-(4-bromophenyl)-pentan-3-ol (2.45 g, 10 mmol) and o-cresol 1.05 mL, 10.2 mmol) in H2O (1.0 mL) chilled to 0° C. was added conc H2SO4 (4.0 g) dropwise. After 1.5 h the reaction mixture was diluted with H2O (50 mL) and extracted with Et2O (2×50 mL). The combined extracts were washed with water, satd NaHCO3, and brine, then dried (anhyd Na2SO4) and concentrated under reduced pressure. The resulting crude product was chromatographed (silica, EtOAC/Hex, 0:100 to 10:90) to afford the title compound (2.1 g, 64% non-optimized) as a colorless liquid: 1H-NMR (CDCl3) δ 7.36 (2H, d, J=8.6), 7.05 (2H, d, J=8.6), 6.83-6.88 (2H, m), 6.67 (1H, d, J=8.1), 4.52 (1H, br s), 2.20 (3H, s), 2.04 (4H, q, J=7.3), 0.61 (6H, t, J=7.3).

Provenance & Evidence