Abstract
The synthetic methods for 3-alkoxy- (IIa, b, c and IIIa, b, c) and hydroxy-2-cyclohexen-1-one oximes (IVa, c) were established. Treatment of dihydroresorcinol (Ia), dihydroorcinol (Ib), dimedone (Ic) and their derivatives with hydroxylamine hydrochloride in methanol, ethanol and water afforded good yields of IIa, b, c, IIIa, b, c and IVa, c. The reaction mechanisms and configurations of the oximes are also mentioned. Inaddition, our experiments revealed that the Gittel's assignment on the product obtained the bytreatment of dimedone (Ic) and NH2OH·HCl in ethanol was erronous, that is, the product was not 3-hydroxy-5, 5-dimethyl-2-cyclohexen-1-one oxime (IVc) assigned by him, but 3-ethoxy-5, 5-dimethyl-2-cyclohexen-1-one oxime (IIIc).
