Acetophenone → 2-(4-Methylphenyl)-1-phenylethan-1-one

Beteiligte Stoffe

Reaktionsschritte

This reaction is carried out in the same manner as the reaction in example 3. The difference is that, the reactants are p-methylphenyl chloride (125.6 mg, 1.0 mmol), acetophenone (300.1 mg, 2.5 mmol), palladium cinnamyl chloride (7.8 mg, 0.015 mmol), 2-Methoxy-6-(N-methyl-N-phenyl-amino)phenyldicyclohexyl)phosphine (18.3 mg, 0.045 mmol), K3PO4:3H2O (665.8 mg, 2.5 mmol) in 3 mL dry toluene at 110° C. for 12 h. 2-(4′-Methylphenyl)-1-phenyl-1-ethanone (140.5 mg) was obtained with a yield of 67% as solid. m.p.: 95.8-96.1° C. (n-hexane); 1H NMR (300 MHz, CDCl3) δ 8.07-8.00 (m, 2H, ArH), 7.62-7.53 (m, 1H, ArH), 7.52-7.43 (m, 2H, ArH), 7.22-7.13 (m, 4H, ArH), 4.27 (s, 2H, CH2), 2.35 (s, 3H, CH3); 13C NMR (75 MHz, CDCl3) δ 197.7, 136.5, 136.3, 133.0, 131.3, 129.3, 129.2, 128.5, 45.0, 21.0; IR (KBr) v (cm−1) 3051, 3024, 2896, 1686, 1592, 1578, 1515, 1448, 1406, 1335, 1221, 1209, 1197, 1181; MS (70 eV, EI) m/z (%): 211 (M++1, 0.65), 210 (M+, 3.47), 105 (100).

Herkunft & Nachweise