Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Rearrangement in Dihydroresorcinol Derivatives. II. Synthesis of 3-Alkoxy and Hydroxy-2-cyclohexen-1-one Oximes
田村 恭光北 泰行松高 佳子寺島 正直
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1971 年 19 巻 3 号 p. 523-528

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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).

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