Benzyl Alcohol → HCID 10878747, compound

Participants

Reaction Conditions

Reaction Steps

Benzyl alcohol (32.90 g, 0.155 mol) was dropped under ice cooling in a suspension of 60% sodium hydride (5.88 g, 0.155 mol) and DMF (150 ml). After emission of hydrogen gas, sodium bromide (9.67 g, 0.094 mol) was added thereto. A DMF solution (15 ml) of (R)-4-chloromethyl-2,2-dimethyl-1,3-dioxolane (11.747 g, 0.078 mol) prepared by the same manner as Example 3 was dropped in it. The temperature was raised to 120° C. and the mixture was stirred for 15 hours. After completion of the reaction the reaction mixture was cooled on ice bath and neutralized with 6% hydrochloric acid. The solution was extracted with ethyl acetate. The organic layer was washed with water and with saturated brine, dried over anhydrous sodium sulfate and condensed in vacuo. The crude product was distilled to give 9.627 g of (S)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane (yield 54%, b.p. 112° C. at 0.3 mmHg).

Provenance & Evidence