4-(6'-Methoxy-3',4'-dihydronaphthalen-1'-yl)butan-2-one and the Derived Guareschi Imide

Abstract

4-(6′-Methoxy-3′,4′-dihydronaphthalen-1′-yl)butan-2-one (6b) was condensed with ethyl cyano-acetate to give a mixture of the geometric isomers of the α, β unsaturated cyano ester (8), reaction of which with the anion derived from cyanoacetamide gave the Guareschi imide (7). Attempts to hydrolyse this to 3-[2′-(6″-methoxy-3″,4″-dihydronaphthalen-1″-yl)ethyl]-3-methylglutaric acid (4) gave only polymeric material.

The preparations of 2,2-ethylenedioxy-4-(6′-methoxynaphthalen-1′-yl)butane (5a) and the corresponding butanone (5b) are also described.