Bromide ion → 3-(3-Methoxyphenyl)-3-hydroxyindan-1-one

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Reaction Steps

m-Methoxyphenyl magnesium bromide (prepared from 10 g of the corresponding bromide and 1.45 g of magnesium turnings in ether) was treated at 0° with a solution of 1,3-indandione (3.5 g) in ether. After stirring at 25° for 4.5 hours, the mixture was quenched with saturated ammonium chloride solution. The layers were separated, the aqueous layer was extracted with ether, and the organic layers were dried (MgSO4) and concentrated. Chromatography of the residue on silica gel provided the title compound as a viscous yellow oil (3.6 g, 59%). NMR and IR spectra were consistent with the assigned structure.

Provenance & Evidence