4-Methoxyphenol → HCID 69693963, compound

HRID 896017Notes

Reaction equation

HRID 896017 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[CH3:10][O:11][C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16](Br)=[CH:15][C:14]=1[CH3:20].C(=O)([O-])[O-].[K+].[K+]>C(OCC)C.[Cu]>[CH3:10][O:11][C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([O:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:15][C:14]=1[CH3:20]

Participants

6

Reactant 3

HCID 90154-MethoxyphenolHCID 11430Potassium CarbonateHCID 22031226Methyl 4-bromo-2-methylbenzoate

Product 1

HCID 69693963HCID 69693963, compoundYield 28.2%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 4-methoxyphenol (12 grams, 52.4 mmol), 4-bromo-2-methylbenzoic acid methyl ester (12 grams, 52 mmol), potassium carbonate (14.5 grams, 105 mmol) and copper powder (3.3 grams, 52 mmol) was stirred at 200° C. for 12 hours. The mixture was cooled to 25° C., diluted with diethylether, and the organic phase was washed twice with water, dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by silica gel chromatography (5% ether in hexanes) afforded 4.0 grams of 4-(4-Methoxy-phenoxy)-2-methyl-benzoic acid methyl ester. MS: 273.2 [M+H]+

Workup

  1. temperatureThe mixture was cooled to 25° C.
  2. washthe organic phase was washed twice with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography (5% ether in hexanes)

Sources & evidence

ORD record
ord-f3d5379c58f443aabd09259f2711f854
Source dataset
uspto-grants-2005_07
Patent number
US06919332B2

Reaction notes

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