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

HRID 595358

Reaktionsgleichung

Reaktionsgleichung von HRID 595358
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](Cl)=[CH:4][CH:3]=1.[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:11])[CH3:10].P.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C(Cl)C=CC1C=CC=CC=1.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 7410AcetophenoneHCID 78104-ChlorotolueneHCID 24404PhosphineHCID 62657Potassium Phosphate, Tribasic

Produkt 1

HCID 2424732-(4-Methylphenyl)-1-phenylethan-1-oneAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 131734589Palladium cinnamyl chlorideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. customThis reaction is carried out in the same manner as the reaction in example 3

Quellen und Nachweise

ORD-Eintrag
ord-d8b400568a7b495ba5fa3000fb3ae126
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09243011B2

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