反应详情

A mixture of 1-methylcyclohexanol (100.00 g, 0.876 mol) and 4-bromophenol (101.01 g, 0.584 mol) in CH2Cl2 (1.0 L) and H2SO4 (44 mL) was heated to reflux for 4 days. The mixture was cooled to RT. The reaction was poured in a separatory funnel and washed with water, 0.5 N NaHCO3 (till neutralized), brine and dried (MgSO4). The mixture was filtered, evaporated and the residue was purified on silica gel (eluant: hexane: CH2Cl2, 4:1) to give a total amount of 2-(1-methylcyclohexyl)-4-bromoanisole as an oil (29.70 g, 13%). 1H NMR (300 MHz, CDCl3): δ 1.30 (s, 3H), 1.30–1.70 (m, 8 H), 2.00–2.15 (m, 2H), 4.87 (s, 1H), 6.54 (d, J=8.4 Hz, 1H), 7.15 (dd, J1=8.4 Hz, J2=2.4 Hz, 1H), 7.36 (d, J=2.4 Hz, 1H).

1. temperaturewas heated
2. temperatureto reflux for 4 days
3. additionThe reaction was poured in a separatory funnel
4. washwashed with water, 0.5 N NaHCO3 (till neutralized), brine
5. dry with materialdried (MgSO4)
6. filtrationThe mixture was filtered
7. customevaporated
8. customthe residue was purified on silica gel (eluant: hexane: CH2Cl2, 4:1)