The Resolution of Two Methoxy-Naphthyl Ethanols.

Various investigations carried out in this laboratory have shown the very pronounced influence exerted by a methoxyl group substituted in the ortho- or para- position of a phenyl radical in conferring alkyl-oxygen fission behaviour in the hydrolysis of carboxylic esters of appropriate alcohols. For example the carboxylic esters of I -phenylethanol show no tendency towards alkyl-oxygen fission yet when a methoxyl group is substituted into the p-position the resulting esters readily exhibit this behaviour Similarly when a methoxyl group is introduced into the 2- or 4- position of benzhydrol the resulting compounds show very pronounced alkyl-oxygen fission behaviour. Similarly 1-1-(1-naphthyl) ethanol shows little or no tendency to alkyl-oxygen fission and part of the object of the present work was to ascertain the extent of the influence of a methoxyl group when substituted in the ortho -position to the sec-alcoholic grouping and compare this with the effect of a methoxyl group substituted in the second nucleus of the naphthyl radical. It is shown that the influence of the ortho-methoxyl group is far greater than that substituted in the second benzene ring as might he anticipated on general grounds - nevertheless its influence is quite pronounced. In marked contrast it is shown that the influence of a methoxyl group in the 4-position of the phenylyl radical is not transmitted to the I-position for the resulting alcohol exhibits no tendency to alkyl-oxygen fission