Oxygen → HCID 53918584, compound

Participants

Reaction Steps

A stream of dry oxygen was passed through a stirred solution (heated at 30°-35° C.) of 1-(2-cyclododecen-1-yl)-2,2,2-trichloroethyl acetate (12 g; 35 m. moles) in methanol (10 ml) and a solution of cupric chloride dihydrate (0.19 g; 1.1 m. moles) and 1,10-phenanthroline hydrate (0.56 g; 2.85 m. moles) in methanol (45 ml) in which sodium (1.39 g; 6.0 m. moles) had been dissolved was added portionwise over a period of 225 minutes. The mixture was then diluted with dilute hydrochloric acid (100 ml), extracted with ether (3×50 ml) and the combined ether extracts were washed with aqueous sodium carbonate solution (50 ml) and water (50 ml). The dried (MgSO4) extract was evaporated and the crude product (4.7 g) distilled to give methyl 2-cyclododecene-1-carboxylate (3.9 g; 56%), b.p. 90°-110° C./0.1 mm. G.L.C. analysis indicated a purity of 85%.

Provenance & Evidence