1-Phenyl-1-propanone → 1-Propanone, 2-(2-methoxyphenyl)-1-phenyl-

HRID 595352Notes

Reaction equation

HRID 595352 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1Cl.[C:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])[CH2:11][CH3:12].C(O[Na])(C)(C)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.COC1C=CC=C(N(C)C2C=CC=CC=2)C=1P(C1CCCCC1)C1CCCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:11]([CH3:12])[C:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13]

Participants

7

Reactant 3

HCID 71481-Phenyl-1-propanoneHCID 130112-ChloroanisoleHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 116443931-Propanone, 2-(2-methoxyphenyl)-1-phenyl-Yield 82.7%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 71725627(2-Dicyclohexylphosphino-3-methoxy-N-methyl-N-phenylbenzenamineCatalystHCID 1140TolueneSolvent

Procedure

This reaction is carried out in the same manner as the reaction in example 3. The difference is that, the reactants are o-methoxyphenyl chloride (144.1 mg, 1.0 mmol), propiophenon (161.3 mg, 1.2 mmol), palladium acetate (6.7 mg, 0.030 mmol), 2-Methoxy-6-(N-methyl-N-phenyl-amino)phenyl(dicyclohexyl)phosphine (18.4 mg, 0.045 mmol), t-BuONa (115.5 mg, 1.2 mmol) in 3 mL dry toluene at 110° C. for 16 h. 2-(2′-Methoxyphenyl)-1-phenyl-1-propanone (198.8 mg) was obtained with a yield of 80% as liquid. 1H NMR (300 MHz, CDCl3) δ 8.04-7.98 (m, 2H, ArH), 7.50-7.42 (m, 1H, ArH), 7.41-7.33 (m, 2H, ArH), 7.24-7.13 (m, 2H, ArH), 6.92-6.86 (m, 2H, ArH), 5.13 (q, J=6.9 Hz, 1H, CH), 3.87 (s, 3H, OCH3), 1.51 (d, J=6.9 Hz, 3H, CH3); 13C NMR (75 MHz, CDCl3) δ 201.2, 155.6, 136.4, 132.4, 130.0, 128.4, 128.2, 127.9, 120.9, 110.7, 55.3, 40.2, 17.5; IR (neat) v (cm−1) 3063, 2974, 2933, 2871, 2837, 1682, 1597, 1584, 1493, 1449, 1371, 1326, 1291, 1245, 1222, 1182, 1113, 1061, 1050, 1028, 1002; MS (70 eV, EI) m/z (%): 241 (M++1, 1.81), 240 (M+, 9.60), 135 (100).

Workup

  1. customThis reaction is carried out in the same manner as the reaction in example 3
  2. customat 110° C.
  3. customfor 16 h

Sources & evidence

ORD record
ord-d67fa053457e4d2db208406d8e6e088a
Source dataset
uspto-grants-2016_01
Patent number
US09243011B2

Reaction notes

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