1,5-Dimethylbicyclo(3.2.1)octan-8-one → 1,5-Dimethylbicyclo[3.2.1]octan-8-one oxime

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Reaction Conditions

Reaction Steps

At 60° C., 91.2 g (0.6 mole) of 1.5-dimethyl-bicyclo[3.2.1]octane-8-one (1) was dripped into a solution of 78.7 g (0.6 mole) hydroxylamin hydrogensulfate and 54.2 g (0.66 mole) sodium acetate in 135 g water. This was stirred for 1 h at 60° C. and then allowed to cool to room temperature and sodium extracted with ether. The combined organic phases were neutralized by washing with a saturated solution of chloride, dried and concentrated by evaporation. 95 g (95%) 2 crystalline solid is obtained. By crystallising 9 g of the raw product from 15 ml ethanol, 8 g 2 are obtained having a m.p. of 129°-130° C. IR: 3400, 3250, 1685, 930 cm-1 (oxim). NMR (CCl4): δ=1.05, s (--CH3, transoid to --C=N--OH), 1.43, s (--CH3, cisoid to -- C=N--OH), 9.03 ppm (--C=N--OH). MS: m/z (%)=167 (M+, 2%), 150(85), 133(15), 123(17), 108(23), 93(100). C10H17ON (M: 167.24)

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