Allyl bromide → 1-[2-(Allyloxy)-4-methylphenyl]ethanone

関与物質

反応手順

To a solution of 1-(2-hydroxy-4-methyl-phenyl)-ethanone (10 g, 67 mmol) in dimethylformamide (100 mL) was added potassium carbonate (18.4 g, 133 mmol), followed by allyl bromide (5.75 mL, 67 mmol). The reaction was stirred at room temperature for 16 hours. The residue was partitioned between ethyl acetate (200 mL) and water (800 mL), the organics were separated, and washed with brine (50 mL), dried over MgSO4 and concentrated in vacuo. After cooling the concentrate to room temperature the title compound crystallised as colourless platelets, 12.40 g, in a 98% yield. LCMS (2 min acidic) 1.20 min 72-100% pure by UV, ES+/AP+ 191. 1HNMR (400 MHz, CDCl3) δ ppm 2.37 (s, 3H), 2.63 (s, 3H), 4.61-4.66 (m, 2H), 5.33 (dq, 1H), 5.44 (dq, 1H), 6.10 (m, 1H), 6.76 (s, 1H), 6.80-6.83 (m, 1H), 7.68 (d, 1H).

情報源と証拠