3-Methoxyphenol → 1-(3-Methoxyphenoxy)-4,4-dimethyl-2-pentanone

HRID 1532169Notes

Reaction equation

HRID 1532169 reaction equation
Br[CH2:2][C:3](=[O:9])[CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=1)[O:18][CH2:2][C:3](=[O:9])[CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 90073-MethoxyphenolHCID 10796Cesium carbonateHCID 2225851-bromo-4,4-dimethylpentan-2-one

Product 1

HCID 224590191-(3-Methoxyphenoxy)-4,4-dimethyl-2-pentanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of the product from Step B (1.626 grams) in dry DMF (18 mL) was combined with 3-methoxyphenol (1.256 grams) and cesium carbonate (3.292 grams). The mixture was stirred for 2.5 hours. The reaction was partitioned between isopropyl acetate and pH4 pthalate buffer. The organic was washed twice with water, dried over magnesium sulfate and filtered. Concentration furnished an oil from which the title compound was isolated by chromatography over silica gel (4:1 hex/ethyl acetate).

Workup

  1. customThe reaction was partitioned between isopropyl acetate and pH4
  2. washThe organic was washed twice with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationConcentration

Sources & evidence

ORD record
ord-572f12b94d8e4977a0a08fa91f3ab9f4
Source dataset
uspto-grants-2001_03
Patent number
US06200998B1

Reaction notes

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