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

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

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).