Acetone → 2,2-Dimethyl-4-((phenylmethoxy)methyl)-1,3-dioxolane

Participants

Reaction Conditions

Reaction Steps

Benzyl alcohol (21.93 g, 0.203 mol) was dropped under ice cooling in a suspension of 60% sodium hydride (3.92 g, 0.103 mol) and DMF (100 ml). After emission of hydrogen gas, therein a DMF solution (10 ml) of 3-chloro-1,2-propanediol (5.692 g, 0.052 mol) was dropped. The reaction temperature was raised to 60° C. and the mixture was stirred under heating for 2 hours. After completion of the reaction the reaction mixture was cooled on ice bath and neutralized with 6% hydrochloric acid. After removal of water and DMF in vacuo, ethyl acetate was added to the residue, the insoluble materials were filtered off and the filtrate was condensed in vacuo. Thereto acetone (500 ml) and p-toluenesulfonic acid (0.386 g) were added and the solution was stirred for 3 hours at 25° C. After the reaction was over, the mixture was neutralized with triethylamine. After stirring for 5 minutes, acetone was removed by distillation. The crude product was distilled to give 5.949 g of 4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane (yield 52%, b.p. 110° C. at 0.3 mmHg).

Provenance & Evidence