2-propylpropane-1,3-diol → 5-Propyl-2-(4-(4-trifluoromethylphenyl)butyl)-1,3-dioxane

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Reaction Steps

2-Propyl-1,3-propanediol 5.90 g (49.9 mmol) and the above 5-(4-trifluoromethylphenyl)pentanal 7.50 g (32.6 mmol) were dissolved in toluene 70 ml, and PTS 1 g was added, and the mixture was refluxed with heating for 3 hours while removing water formed with Dien-Stark. The reactant was washed with a saturated sodium bicarbonate aqueous solution, and then with saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (eluent: toluene), and recrystallized twice from ethanol to obtain 5-propyl-2-(4-(4-trifluoromethylphenyl)butyl)-1,3-dioxane 5.55 g (16.7 mmol). The yield was 51.2% from 5-(4-trifluoromethylphenyl) pentanal.

Provenance & Evidence