Oxygen → HCID 11011719, compound

Participants

Reaction Steps

A 125 mL Erlenmeyer flask equipped with a magnetic stirring bar was chargedwith 10.0 g (48.4 mmoles) of 92% 3-t-butylperoxy-1,3-dimethylbutanol, 7.8 g(77.2 mmoles) of triethylamine, 0.1 g (0.08 mmole) of 4-dimethylaminopyridine and 30 g of dry ethyl acetate. A clear solution resulted at room temperature. To this vigorously stirred solution at room temperature was slowly added a solution consisting of 7.0 g (50.2 mmoles) of ethyl oxalyl chloride and 10 g of dry ethyl acetate over a period of 20minutes. A precipitate immediately formed and the flask became warm. It wasnecessary to cool the flask in order to maintain the temperature around room temperature. After a total reaction period of 60 minutes, the reaction mass was transferred to a separatory funnel, 100 mL of water was added to the reaction mass and shaken. The aqueous phase was separated anddiscarded. The organic phase was washed once with aqueous 10% HCl solution,twice with water and once with dilute aqueous NaHCO3 solution. The resulting solution was dried over about 10% by weight of anhydrous MgSO4, and, after separation of the spent desiccant by filtration, the solvent was removed in vacuo leaving 13.9 g (99% of theory, uncorrected) of a clear yellow liquid. The product contained 5.79% active oxygen (theory, 5.51%), therefore, compound I-1, was obtained with an assay of 100% and in a corrected yield of 99%. Gas chromatographic analysis showed that the product contained less than 0.1% of 3-t-butylperoxy-1,3-dimethylbutanol, the starting material. An infrared (IR) spectrum of the product showed carbonyl bands at 1770 cm-1 and 1745 cm-1 and a peroxide (--OO--) band at 870 cm-1.

Provenance & Evidence