Methyl iodide → 4-(4-Methoxyphenyl)cyclohexanone

Participants

Reaction Steps

To a solution of 4-(4-hydroxyphenyl)cyclohexanone (1 g, 5.26 mmol) in DMF (50 ml) was added cesium carbonate (3.00 g, 9.20 mmol) followed by methyl iodide (0.411 ml, 6.57 mmol). The reaction was stirred at room temperature for 1 hour and then diluted with ethyl acetate (100 mL), washed with water (3×50 mL), and brine (50 mL). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel with 0 to 100% EtOAc/hexanes afforded 4-(4-methoxyphenyl)cyclohexanone. 1H NMR (CDCl3, 500 MHz) δ 7.16 (d, J=8.4 Hz, 2H), 6.87 (d, J=8.7 Hz, 2H), 3.80 (s, 3H), 2.99 (m, 1H), 2.45-2.55 (m, 4H), 2.16-2.23 (m, 2H), 1.86-1.96 (m, 2H).

Provenance & Evidence