Sodium Hydroxide → 9,12-Octadecadienamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-, (E,E)-

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Reaction Steps

N-vanillyl-(E,E)-9,12-octadecadienamide was synthesized by the following method: ##STR5## Specifically 6.88 g of 4-hydroxy-3-methoxybenzylamine-HCl was dissolved in 50 ml of tetrahydrofuran (THF), and stirred. Added were 14 ml of a 5N solution of NaOH, and the mixture was stirred for 10 to 15 minutes. Then 10.6 g of (E,E)-9,12 octadecadienoyl chloride (linoelaidoyl chloride), dissolved in THF, was added dropwise. The mixture was then stirred overnight, allowing it to come to room temperature. The solvent was evaporated and the residue partitioned between ethyl ether and water. The organic phase extract was washed with HCl, sodium bicarbonate, water, and brine, and then dried and filtered. 16 g of crude N-vanillyl-(E,E)-9,12)-octadecadienamide was obtained. Purification by recrystallization from ether and pentane gave 9.4 g of analytically pure product. Its structure was confirmed via nuclear magnetic resonance and infrared spectroscopy.

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