Sodium hydride → HCID 54277596, compound

Participants

Reaction Steps

To a suspension of sodium hydride (1.9 g) in ether (40 ml) while cooling with ice, ethyl isobutyroylacetate (5.2 g) is added, and 1-bromo-8-acetoxy-2,6-dimethyl-2,6-octadiene (8 g) is dropwise added thereto. The reaction is carried out with reflux for 8 hours. The ether layer is separated from the reaction mixture, washed with water, dried and evaporated. The oily product (9.9 g) is added to a solution of potassium hydroxide (6.3 g) ethanol (120 g), and refluxing is continued for about 1 hour. The resultant mixture is added to the ice water, made acidic with 10% sulfuric acid and extracted with ether. The ether extract is washed with saturated aqueous solution of sodium chloride, aqueous solution of sodium hydrogen carbonate and water in order, and then the ether is evaporated therefrom. The residue (7.2 g) is dissolved in benzene and purified by chromatography on silica gel to give 3,7,11,-trimethyl-2,6-dodecadien-10-on-1-ol (6.2 g). NMR (carbon tetrachloride): δ 1.05 (d), 1.59 (s), 2.0 (s), 21.-2.7 (m), 3.52 (s), 3.95 (d), 4.8-5.4 (m).

Provenance & Evidence