3-(N,N,N-trimethylammonio)-1-(3,4,5-trimethoxyphenyl)propan-1-one iodide → 2-Propen-1-one, 1-(3,4,5-trimethoxyphenyl)-

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The above iodide (355.9 g, 0.87 mol) was suspended in a mixture of water (3.56 L) and ethyl acetate (2.54 L) and heated under reflux with rapid stirring for 2-3 hours. The mixture was cooled and the pale yellow organic layer was removed. Fresh ethyl acetate (2 L) was added and the mixture was again heated under reflux for 1 hour and the process was repeated once again. The organic extracts were combined, washed with brine, dried (MgSO4), and evaporated to a yellow oil which was crystallized from hexane-ethyl ether to give 1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one: mp 46°-47° C.; NMR (CDCl3) δ 3.94 (s, 3 OCH3), 5.92 (2 d, J=1.5 & 9.0 Hz, CH=CH2), 6.44 (2 d, J=1.5 & 16 Hz, CH=CH2), 7.18 (2 d, J=9.0 & 16 Hz, CH= CH2), 7.28 (ArH).

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