4'-Hydroxyacetophenone → HCID 13340058, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4′-hydroxyacetophenone (10.6 g, 77.7 mmol) in 600 mL MeOH and 15 mL H2O at room temperature was added Cs2CO3 (25.6 g, 1.01 eq). The reaction mixture immediately turned yellow and was then stirred for 40 min. The MEOH was removed in vacuo, and the remaining H2O was removed azetropically with 5×100 mL toluene. The resulting yellow solid was suspended in DMF (450 mL) and treated with (bromomethyl)cyclohexane (13.0 mL, 1.2 eq). The reaction mixture was heated to 90° C. and stirred overnight. The reaction mixture was then cooled to room temperature, poured into 500 mL of ice water and extracted with Et2O. The Et2O extract was dried over MgSO4 and concentrated in vacuo to a yellow oil, which smelled of the starting bromide. The bromide was distilled off at 50° C. under high vacuum until the bottoms reached a constant weight (13.96 g, 77%). This oil solidified to a white solid upon standing. 1H NMR (300 MHz CDCl3): 7.91 (2H, d, J=8.9 Hz), 6.90 (2H, d, J=8.8 Hz), 3.81 (2H, d, J=6.1 Hz), 2.55 (3H, s), 1.8 (6H, m), 1.2 (3H, m), 1.1 (2H, m).

Provenance & Evidence