Peracetic Acid → 2-(Prop-2-en-1-yl)cyclododecan-1-one

Participants

Reaction Steps

22.0 g (100 mmole) of 2-allyl-cyclododecanone--Helv. Chim. Acta 54, 2889 (1971)--in admixture with 13.2 g (12.2 mmole) of thiophenol and 0.3 g of α,α'-azoisobutyronitrile were heated at 100° for 10 hours, an additional amount of 0.6 g of α,α'-azoisobutyronitrile being added over this period, portionwise, to the reaction mixture. After elimination of the excess of thiophenol and unreacted 2-allyl-cyclododecanone (2.25 g) by distillation (170°/0.05 Torr) the reaction mixture was diluted with 300 ml of trichloroethane and cooled to 0°. 90.4 g (475 mmole) of 40% peracetic acid were then progressively added to the above solution under good stirring (reaction temperature: 30°-40°). After addition of 7.5 g (53 mmole) of BF3.Et2O, the resulting mixture was further stirred for 10 days at 50°, 4 portions each of 11.3 g (60 mmole) of 40% peracetic acid being added thereto over this period. After cooling to 20°, the reaction mixture was poured onto crushed ice and then brought to pH 8 by the addition of 10% aqueous sodium hydroxide. After washing with a 10% solution of NaHSO3 in water, then with H2O, the organic phase was dried over Na2SO4 and evaporated. The obtained residue was finally purified by column chromatography (silicagel-eluent: 50/50 mixture of petrol ether and ethyl acetate) to afford 27.7 g (81% yield based on transformed 2-allyl-cyclododecanone) of the title compound (purity 90%).

Provenance & Evidence