Diethyl Ether → HCID 86737257, compound

Participants

Reaction Steps

A mixture of 5-ethylenedioxy-1-hexene (6.0 g.), osmium tetroxide (0.5 g.), ether (150 ml.) and water (150 ml.) is treated portionwise with sodium metaperiodate (19.3 g.) so that the reaction temperature does not exceed 30°. After the addition of the periodate, a voluminous white solid precipitates out. The mixture is stirred 2.5 hrs. at room temperature, then filtered, and the solid portion is washed with more aqueous ether. The aqueous portion of the filtrate is separated and extracted with three portions of methylene chloride. The combined organic phases are dried with magnesium sulfate, filtered, and evaporated in vacuo. Distillation of the residue yields 4-ethylenedioxy-pentanal (65% yield) b.p. 56°-58°/10.5 m nmr (CDCl3) δ: 1.27 (s, CH3), 2.04-2.80 (m, --CH2 --CH2 --); 3.9 (s, --OCH2 --CH2 --O), 9.73 (t, O=C--H). IR (film) μ: 3.66; 3.79.

Provenance & Evidence