Methyl cyclohexenyl ether, hydrolysis

Fig. 4.7. Br0nsted relation for the hydrolysis of methyl cyclohexenyl ether. (Reproduced from reference 21 by permission of the American Chemical Society.)...

Br0nsted relation for hydrolysis of methyl cyclohexenyl ether... 

The 4-methoxy group present in the des bases C and D may be present in tazettine itself or introduced in the course of the methylation with dimethyl sulfate. Kondo and co-workers preferred the latter alternative they formulated tazettine as an enol which was converted to an enol methyl ether in the preparation of methyltazettine methiodide. Such a concept is inadmissible since 0-acetyltazettine does not have the spectral or chemical properties of an enol acetate. Further, the hydrolytic conditions required to convert methyltazettine methochloride to tazettine methochloride (in poor yield) were more vigorous than those usually required for the hydrolysis of a 1-cyclohexenyl methyl ether. It is evident then that the methoxyl group of tazettine is in the 4-position of CXXV, and it follows that the double bond is located in the 2,3-position. 

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See also in sourсe #XX -- [ ]

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