Water → 2-(3-Bromopropyl)-1,3-dioxolane

Participants

Reaction Conditions

Reaction Steps

At -70° C., 50 ml of a 1.2-molar solution of diisobutyl aluminum hydride in toluene is added dropwise gradually to a solution of 9.6 g of the ethyl ester of bromobutyric acid in 595 ml of toluene; the mixture is stirred for 15 minutes at -70° C. and then combined dropwise with 10 ml of isopropyl alcohol and 25 ml of water. The mixture is agitated for 2 hours at room temperature, filtered, the filtrate dried with magnesium sulfate and evaporated under vacuum at 25° C. The residue is dissolved in 500 ml of toluene, 10 ml of ethylene glycol and 100 mg of p-toluenesulfonic acid are added, and the mixture is refluxed for 6 hours with the use of a water trap. Subsequently the mixture is diluted with 500 ml of ether, shaken once with a 5% sodium bicarbonate solution and three times with water, the organic extract is dried with magnesium sulfate and concentrated under vacuum at 30° C. Distillation of the residue at 0.6 torr and 43°-45° C. yields 6.8 g of 2-(3-bromopropyl)-1,3-dioxolane as a colorless liquid.

Provenance & Evidence