Sodium Hydroxide → 2-Ethyl-6-methoxybenzaldehyde

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A solution of 1.0 g (E)-[1-(2-ethyl-6-methoxy-phenyl)-methylidene]-(1-isopropyl-2-methyl-propyl)-amine in 1 ml THF and 0.19 ml 4N HCl was heated to reflux for 1 hour then cooled to ambient temperature and poured onto a 1N aqueous NaOH solution. The aqueous phase was extracted with ethyl acetate, the combined extracts washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by flash-chromatography on silica gel with a heptane/ethyl acetate gradient as eluent: 0.50 g 2-ethyl-6-methoxy-benzaldehyde as colourless oil: MS (EI): 261.2 (M+.), 218.2 ((M-((CH3)2CH))+., 100%).

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