1,1,2-Trichloroethane → HCID 54150769, compound

Participants

Reaction Steps

2-(3-Phenylsulfonyl-prop-1-yl)-cyclododecanone used hereinabove (Examples 1 and 2) as starting material was prepared as follows: 222 g (1 mole) of 2-allyl-cyclododecanone-Helv. 54, 2889 (1971)--in admixture with 132 g (1.2 mole) of thiophenol and 3.0 g of α,α'-azoisobutyronitrile were heated at 100° for 10 hours, an additional amount of 6.0 g of α,α'-azoisobutyronitrile being added over this period, portionwise, to the reaction mixture. After dilution with an excess amount of trichloroethane and cooling in an ice-bath, 376 ml (2.6 mole) of 40% peracetic acid were progressively added to the reaction mixture, under good stirring (reaction temperature: 25°-30°). After treatment with an excess amount of an aqueous solution of NaHSO3 (elimination of peroxides), a 10% solution of NaOH in water was added thereto until pH 8-9 (temperature ca. 10°). After extraction with methylene chloride (2×300 ml), successive washings with water and brine, drying over Na2SO4, evaporation and crystallization of the crude residue in a CH2Cl2 /diethyl ether/petrol ether mixture, there were finally isolated 332 g (91% yield) of the desired compound, m.p. 97°-102°.

Provenance & Evidence