FIELD: chemistry.
SUBSTANCE: invention relates to a method of producing ω-iodo-aliphatic carboxylic acids and esters thereof. The method involves splitting aliphatic cyclic ketones such as cyclohexanone, cycloheptanone or 4-methylcyclohexanone, under the action of hydrogen peroxide in the presence of a catalyst and iodine compounds at room temperature. The catalyst used is copper (I) chloride; production is carried out with radio of cyclic ketone: hydrogen peroxide: copper (I) chloride of 1:5:0.1, while stirring for 10-20 hours, in the presence of methanol or ethanol solutions of iodine; iodine is taken in an amount which is such that the ratio of cyclic ketones to iodine is 1:0.5. In order to extract and separate the end products, a saturated solution of sodium bicarbonate is added to the reaction mass, wherein ω-iodo-aliphatic carboxylic acids are transferred into the aqueous layer in form of sodium salts, and esters thereof are easily separated by extracting the aqueous layer with ethyl acetate. The ethyl acetate extraction is then dried with anhydrous sodium sulphate; ethyl acetate is evaporated and esters of ω-iodo-aliphatic carboxylic acids are obtained. In order to extract only ω-iodo-aliphatic carboxylic acids, the reaction mass, which contains a mixture of acids and their esters, is extracted with methylene chloride, water and trifluoroacetic acid are added, stirred at room temperature for 20-24 hours and the solvent is then evaporated.
EFFECT: improved method of producing ω-iodo-aliphatic carboxylic acids and esters thereof.
3 cl, 12 dwg, 17 ex
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Authors
Dates
2013-09-27—Published
2012-08-21—Filed