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

HRID 613417Notes

Reaction equation

HRID 613417 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-6ef3253ee57342a08b5f9df8295e6386
Source dataset
uspto-grants-1999_12
Patent number
US06008237

Reaction notes

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