Hydrochloric Acid → (E, E)-3,7,11,15-Tetramethyl-6,10,14-hexadecatrienonitrile

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Reaction Steps

To the entirety of the product obtained in the above (a) step, there were added 29 g. of sodium hydroxide and 100 ml. of propylene glycol, and the mixture was stirred at room temperature for 10 min. The reaction mixture was made acidic by addition of 6N hydrochloric acid, and was then extracted with benzene. The extract was then washed with water and dried. The solvent was then removed by evaporation. The obtained oily product was dissolved in 100 ml. of pyrydine, and the resulting solution was refluxed for 2 hours after addition of 0.5 g. of copper powder. Subsequently, the copper powder was removed by filtration and the solvent was removed by evaporation. The residue was dissolved in n-hexane, washed with water and dried. The solvent was then removed by evaporation and the residue was purified by silica gel column chromatography to obtain 34 g. of the desired oily product.

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