Acetone → 1-(p-Methoxyphenyl)-2-propanone

Participants

Reaction Steps

This reaction is carried out in the same manner as the reaction in example 3. The difference is that, the reactants are p-methoxyphenyl chloride (143.2 mg, 1.0 mmol), palladium cinnamyl chloride (7.9 mg, 0.015 mmol), 2-Methoxy-6-(N-methyl-N-phenyl-amino)phenyldicyclohexyl)phosphine (24.5 mg, 0.060 mmol), Cs2CO3 (651.0 mg, 2.0 mmol) in 4.0 mL acetone at 90° C. for 12 h. 1-(4′-Methoxyphenyl)-2-propanone (137.9 mg) was obtained with a yield of 84% as liquid. 1H NMR (300 MHz, CDCl3) δ 7.15-7.07 (m, 2H, ArH), 6.92-6.82 (m, 2H, ArH), 3.79 (s, 3H, OCH3), 3.63 (s, 2H, CH2), 2.13 (s, 3H, COCH3); 13C NMR (75 MHz, CDCl3) δ 206.8, 158.5, 130.3, 126.1, 114.0, 55.1, 50.0, 29.0; IR (neat) v (cm−1) 3002, 2957, 2935, 2911, 2837, 1713, 1612, 1584, 1514, 1464, 1442, 1423, 1356, 1301, 1249, 1179, 1158, 1109, 1034; MS (70 eV, EI) m/z (%): 165 (M++1, 2.58), 164 (M+, 23.60), 121 (100).

Provenance & Evidence