tert-Butanol → 2-tert-Butyl-4-(2-methylbutan-2-yl)phenol

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Reaction Steps

4-t-amylphenol (80 g, 0.49 mole) was dissolved in 200 ml anhydrous trifluoroacetic acid (TFA). T-butyl alcohol (39 g, 0.53 mole) was added with stirring. The mixture was stoppered and stirred for 19 hours at ambient (~22° C.) temperature. The solution was then poured into 400 ml of 1M NaOH, and the resulting upper organic layer was isolated in a separatory funnel. The crude product was dried over anhydrous magnesium sulfate. The product, 4-t-amyl-2-t-butylphenol, was purified by eluting 35 g of the mixture the mixture with 60:40 hexanes:dichloromethane (v/v) in a 5×20 cm silica column and eluted with 300 to 700 ml of solvent and collected in aliquots of 50 ml. Aliquots showing a single spot by Thin Layer Chromatography (TLC) (on silica eluted with 60:40 hexanes:dichloromethane (v/v)) were combined and rotoevaporated to a thick syrup. The yield was 39%.

Provenance & Evidence