Anisole → 2-[1'-Hydroxy-1'-(3-pyridyl)methyl]-4-tert-butylanisole

Participants

Reaction Conditions

Reaction Steps

270 mg of magnesium was suspended in 2 ml of anhydrous diethyl ether and 0.5 ml of a solution of 2-iodo-4-tert-butylanisole (prepared by dissolving 2.90 g of the anisole in 5 ml of diethyl ether), followed by warming the mixture to initiate the reaction. Upon addition of the remaining ethereal solution of the anisole, the mixture began to reflux. The mixture was refluxed for 30 minutes and then cooled to 0° C., and 1.03 ml of nicotinaldehyde dissolved in 5 ml of diethyl ether was added dropwise to the mixture. After stirring for one hour at 0° C., a saturated aqueous solution of ammonium chloride was added to the mixture which was then extracted with ethyl acetate. The ethyl acetate layer was washed successively with water and an aqueous sodium chloride solution, dried and concentrated. The residue was chromatographed on silica gel column using a mixed solvent of methylene chloride and ethyl acetate (1:1 by volume) as an eluting agent to give 1.76 g of the title compound having the following physical properties.

Provenance & Evidence