Water → 2,2-Ethylenedioxy-10-methyl-6-oxa-9-undecene

Participants

Reaction Steps

14 g of sodium hydride in a 50% suspension in oil were added to a solution of 28 g of 4-methyl-3-pentenol [Julia et al, Bull. Soc. Chim., (1960), p. 1072] in 250 ml of dimethylformamide and after stirring the mixture for 1 hour, 66 g of 5-bromo-2,2-ethylenedioxy-pentane were added thereto while keeping the temperature below 35° C. The mixture was stirred at room temperature for 17 hours and the reaction mixture was then poured into water. The mixture was extracted with petroleum ether (b.p.= 40°-75° C.) and the organic phase was washed with water, dried over sodium sulfate and evaporated to dryness. The residue was rectified to obtain 20 g of 2,2-ethylenedioxy-10-methyl-6-oxa-9-undecene in the form of a colorless liquid with a boiling point of 75° C. at 0.05 mm Hg.

Provenance & Evidence