2-Pentyl-1,3-propanediol → 4-(5-Pentyl-1,3-dioxane-2-yl)cyclohexanecarboxylic acid methylester

Participants

Reaction Steps

2-Pentyl-1,3-propanediol 17.0 g (116 mol) and 4-formylcyclohexane carboxylic acid methyl ester 18.8 g (111 mmol) were dissolved in toluene 120 ml, and PTS 1.0 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/ethyl acetate=4/1) to obtain 4-(5-pentyl-1,3-dioxane-2-yl)cyclohexanecarboxylic acid methylester 28.2 g (94.5 mmol). The yield was 85.1% from 4-formylcyclohexanecarboxylic acid methylester.

Provenance & Evidence