Potassium Cyanide → (5-Tert-butyl-2-methoxyphenyl)acetonitrile

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Reaction Steps

Potassium cyanide (2.96 g) was added to a solution of 2-bromomethyl-4-tert-butyl-1-methoxybenzene (7.78 g) in dimethyl sulfoxide (50 mL), and the mixture was stirred at room temperature for 16 hours. Ice and tert-butyl methyl ether were added to the reaction solution, and the organic layer was separated. The aqueous layer was reextracted with tert-butyl methyl ether. The combined organic layers were sequentially washed with water (twice) and brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: heptane→ethyl acetate:heptane=1:49). The target fraction was concentrated. The resulting residue was triturated with hexane to obtain 1.90 g of the title compound. The trituration mother liquor was concentrated. Then, the resulting residue was triturated with hexane to obtain 0.47 g of the title compound. The property values of the compound are as follows.

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