4-Methoxyphenol → 1-Methoxy-4-(4-methylphenoxy)benzene

HRID 1909623Notes

Reaction equation

HRID 1909623 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].I[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1>O1CCOCC1.Cl.CN(C)CC(O)=O>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 90154-MethoxyphenolHCID 10796Cesium carbonateHCID 122074-Iodotoluene

Product 1

HCID 6118401-Methoxy-4-(4-methylphenoxy)benzeneYield 177.4%

Reagents, catalysts & solvents 2

HCID 75605N,N-Dimethylglycine hydrochlorideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Following the general procedure for Example 11 (step 1), N,N-dimethylglycine hydrochloride (0.03 g, 0.22 mmol), cesium carbonate (1.59 g, 4.88 mmol) and Cu(I) iodide (0.02 g, 0.09 mmol) were added to a solution of 4-iodotoluene (0.8 g, 3.67 mmol) and 4-methoxyphenol (0.3 g, 2.42 mmol) in dioxane (10 mL) to afford the title compound (0.92 g, 100%) as a brown oil.

Sources & evidence

ORD record
ord-621a44a36a6c4eda902019efcc2db40d
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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