Dicyclohexylcarbodiimide → HCID 54346421, compound

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Reaction Steps

Then, 300 mg of 4-hydroxyphenyl 4-dodecyloxy-3-chlorobenzoate, 300 mg of β-tetrahydropyranyloxynonanoic acid, 250 mg of dicyclohexylcarbodi-imide and 25 mg of 4-pyrrolidinopyridine were dissolved in methylene chloride, and reaction was carried out at room temperature with stirring overnight. The thus-obtained solution was diluted with ethyl acetate, and the dilution was washed with a 0.5N aqueous solution of hydrochloric acid, a saturated aqueous solution of sodium chloride, a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride in succession, dehydrated on anhydrous magnesium sulfate and concentrated. The intended product was isolated by the silica gel column chromatography using a mixed solvent of n-hexane and chloroform. The isolated product was dissolved in ethanol, 20 mg of pyridinium p-toluenesulfonate was added to the solution, and the mixture was stirred at 50° C. for 1 hour. The thus-obtained solution was diluted with ethyl acetate again, and the dilution was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride in succession, dehydrated on anhydrous magnesium sulfate and concentrated. The intended product was isolated by the silica gel column chromatography using a mixed solvent of n-hexane and chloroform and recrystallized from ethyl acetate to obtain 150 mg of 4-(β-hydroxynonylcarboxy)phenyl 4-dodecyloxy-3-chlorobenzoate. By the NMR spectrum analysis and elementary analysis, it was confirmed that the obtained product was the intended compound. The NMR spectrum of the obtained compound is shown in FIG. 2, and the elementary analysis values are shown below.

Provenance & Evidence