Syntheses in the Isocamphane Series, XV. The Isocamphaneanalogous Mandelic Acid

Article abstract of DOI:10.1007/BF00901831

The synthesis of some new potentially, nitrogenefree spasmolytics is described.Formally the benzene nucleus in some mandelic acid esters, known by their spasmolytic activity, is substituted for the isocamphane bicyclus by a) SeO2 oxidation of 1-(3,3-Dimethyl-2-exo-norbornyl)-ethanone (5) to the corresponding ketoaldehyde 6, b) oxidation of 6 to the isocamphane analogous mandelic acid 4 and c) esterification of derivatives of 4 with isoamylalcohol and benzylalcohol.Attemps to dehydrate the methylester 7 to camphenylideneacetic acid methylester (12) by various methods failed, probably because of the ring strain. - Keywords: Camphenylideneacetic acid; Dehydration; Dehydrohalogenation; Esterification; α-Hydroxy acid, with norbornane skeleton; Riley oxidation; Spasmolytics