Ethyl Acetate → 2-Methyl-beta-[[4-(tetradecyloxy)phenyl]methyl]-1,3-dioxolane-2-propanol

Participants

Reaction Steps

To a suspension of about 2.38 g of lithium aluminum hydride in about 40 ml of ether was added dropwise, over about 1/2 hour, a solution of about 20.5 g of 2-methyl-α-[[4-(tetradecyloxy)phenyl]methyl]-1,3-dioxolane-2-propanoic acid, ethyl ester in about 70 ml of ether at about 0° C. The mixture was stirred about 1/2 hour at room temperature, recooled to about 0° C. and about 10 ml of ethyl acetate, about one ml of water, about 2 ml of about 15% sodium hydroxide and about 3 ml of water were added dropwise. The mixture was filtered through celite, the solids were washed with ether and the ether removed from the combined solutions, which was then purified by HPLC, using the system hexane:ethyl acetate (about 3:7), giving a colorless oil which solidified on standing, giving about 15.28 g of the desired title compound, mp 28°-29° C.

Provenance & Evidence