SyntheticPage 719
Published Feb 27, 2014
Procedure
An oven dried 50 ml round bottom two necked flask, equipped with a spin bar, a septa, a water condenser and a Nitrogen inlet at the top, was charged with 12.5 mL of anhydrous ethanol and 1.03 g (9.6 mmole) of freshly distilled piconilaldehyde. After mixing, 2.0 mL (10.6 mmole) of 2,6-diisopropylaniline were added through the septa with the aid of an hypodermic syringe and the reaction mixture was brought to reflux using a heating mantle. Reflux was kept for an hour and then the system was let to cool down to room temperature. Solvent and reagent excess were removed by means of a rotatory evaporator to give a yellow solid in quantitative yield. The product is sufficiently pure for most purposes but it may be recrystallized from n-pentane at -25oC to give yellow crystals with yields oscillating from 80-85%.
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