3-Methylacetophenone → 2-(4'-Methoxyphenyl)-1-(m-tolyl)-1-ethanone

HRID 595360Notes

Reaction equation

HRID 595360 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](Cl)=[CH:5][CH:4]=1.[C:10]1([CH3:19])[CH:15]=[CH:14][CH:13]=[C:12]([C:16](=[O:18])[CH3:17])[CH:11]=1.P>C1(C)C=CC=CC=1.C(Cl)C=CC1C=CC=CC=1.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:17][C:16]([C:12]2[CH:11]=[C:10]([CH3:19])[CH:15]=[CH:14][CH:13]=2)=[O:18])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 114553-MethylacetophenoneHCID 121674-ChloroanisoleHCID 24404Phosphine

Product 1

HCID 610567072-(4'-Methoxyphenyl)-1-(m-tolyl)-1-ethanoneYield 74%

Reagents, catalysts & solvents 2

HCID 131734589Palladium cinnamyl chlorideCatalystHCID 1140TolueneSolvent

Procedure

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 (141.7 mg, 1.0 mmol), 1-(m-tolyl)ethanone (336.2 mg, 2.5 mmol), palladium cinnamyl chloride (7.8 mg, 0.015 mmol), 2-Methoxy-6-(N-methyl-N-phenyl-amino)phenyldicyclohexyl)phosphine (18.4 mg, 0.045 mmol), K3PO43H2O (664.9 mg, 2.5 mmol) in 3 mL dry toluene at 110° C. for 23 h. 2-(4′-Methoxyphenyl)-1-(m-tolyl)-1-ethanone (176.4 mg) was obtained with a yield of 74% as solid. m.p.: 56.7-57.8° C. (n-hexane); 1H NMR (300 MHz, CDCl3) δ 7.82-7.75 (m, 2H, ArH), 7.36-7.27 (m, 2H, ArH), 7.20-7.10 (m, 2H, ArH), 6.88-6.79 (m, 2H, ArH), 4.18 (s, 2H, CH2), 3.73 (s, 3H, OCH3), 2.37 (s, 3H, ArCH3); 13C NMR (75 MHz, CDCl3) δ 198.0, 158.3, 138.2, 136.4, 133.7, 130.3, 128.9, 128.3, 126.4, 125.7, 113.9, 55.0, 44.4, 21.2; IR (KBr) v (cm−1) 3034, 2999, 2933, 2835, 1694, 1682, 1614, 1585, 1515, 1463, 1301, 1282, 1246, 1178, 1156, 1107, 1035, 1000; MS (70 eV, EI) m/z (%): 241 (M++1, 1.89), 240 (M+, 10.02), 119 (100); Anal. Calcd. for C16H16O2: C, 79.97; H, 6.71. Found: C, 79.71; H, 6.69.

Workup

  1. customThis reaction is carried out in the same manner as the reaction in example 3
  2. customat 110° C.
  3. customfor 23 h

Sources & evidence

ORD record
ord-953723168c554a60bbf8c0bde96061e1
Source dataset
uspto-grants-2016_01
Patent number
US09243011B2

Reaction notes

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