4-Chloroanisole → 1-Propanone, 1,2-bis(4-methoxyphenyl)-

HRID 595350Notes

Reaction equation

HRID 595350 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](Cl)=[CH:5][CH:4]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:21])[CH2:19][CH3:20])=[CH:14][CH:13]=1.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>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:21])[CH:19]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH3:20])=[CH:14][CH:13]=1

Participants

7

Reactant 3

HCID 121674-ChloroanisoleHCID 671444-PropanoylanisoleHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 111293751-Propanone, 1,2-bis(4-methoxyphenyl)-Yield 100.7%

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 p-methoxyphenyl chloride (142.7 mg, 1.0 mmol), 1-(4-methoxyphenyl)-1-propanone (195.8 mg, 1.2 mmol), palladium acetate (6.6 mg, 0.029 mmol), 2-Methoxy-6-(N-methyl-N-phenyl-amino)phenyl(dicyclohexyl)phosphine (18.2 mg, 0.045 mmol), t-BuONa (115.9 mg, 1.2 mmol) in 3 mL dry toluene at 110° C. for 18 h. 1,2-Di(4′-methoxyphenyl)-1-propanone (272.1 mg) was obtained with a yield of 100% as liquid. 1H NMR (300 MHz, CDCl3) δ 7.99-7.92 (m, 2H, ArH), 7.24-7.18 (m, 2H, ArH), 6.87-6.79 (m, 4H, ArH), 4.61 (q, J=6.9 Hz, 1H, CH), 3.76 (s, 3H, OCH3), 3.71 (s, 3H, OCH3), 1.50 (d, J=6.9 Hz, 3H, CH3); 13C NMR (75 MHz, CDCl3) δ 198.9, 163.0, 158.2, 133.8, 130.8, 129.2, 128.5, 114.1, 113.5, 55.1, 54.9, 46.3, 19.4; IR (neat) v (cm−1) 2969, 2932, 2837, 1668, 1600, 1574, 1514, 1455, 1419, 1371, 1303, 1258, 1169, 1114, 1032; MS (70 eV, EI) m/z (%): 270 (M+, 4.28), 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 18 h

Sources & evidence

ORD record
ord-dd7d923be98042cc949c33713958de55
Source dataset
uspto-grants-2016_01
Patent number
US09243011B2

Reaction notes

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