Hydrochloric Acid → 2-Pentyl-1,3-propanediol

Participants

Reaction Steps

35 g (0.92 mol) of lithium aluminum hydride was dispersed in 420 cm2 of anhydrous tetrahydrofuran (THF) and 193 g (0.84 mol) of diethyl pentylmalonate was added drop-wise to the dispersion while stirring at a speed to gently reflux the THF. The solution was refluxed and stirred for 3 hours. The product of the reaction was cooled with water and THF containing 10% water was added until the mixture ceased to foam. 500 cm2 of concentrated hydrochloric acid was added. The oily layer was separated and the water layer was extracted three times with 200 cm3 of ether. The oily layer and the ether layers were combined and washed with a saturated aqueous solution of sodium chloride. The ether layer was dried with anhydrous sodium sulfate and boiled to distil off the ether. The residue of the distillation was subjected to vacuum distillation (b.p. 120° C./2 Torrs) to yield 83 g (0.57 mol) of 2-pentylpropane-1,3-diol.

Provenance & Evidence