I. VAPOR-PHASE OZONIZATION OF DIPENTENE AND d-LIMONENE With the exception of patents granted to Knox (1) and Rogers (2) for vapor-phase ozonization of pinene and cinnamic aldehyde, no reports were

Vol. 66 parison with material prepared by a conventional synthesis involving the cyclization of m-hydroxyhydrocinnamic acid. Condensation of 2-hydroxymethylene-5-methoxyhydrindone-l with hydroxylamine hydrochloride in acetic acid yields, instead of the expected nitrile, a dimolecular condensation product which is probably bis-(5methoxy -1 -keto -2 -hydrindylidenemethyl)hydroxylamine. Alkaline hydrolysis of the latter in the presence of hydroxylamine gives ß-(2carboxy-5-methoxyphenyl)-propionic acid. This acid is also obtained on alkaline cleavage of 2-cyano-5-methoxyhydrindone-l which can be prepared from 5-methoxyhydrindone-l through the 2-bromo derivative.Oxidation of 6-methoxytetralin with lead tetraacetate gives the 1-acetoxy derivative in 62% yield. The latter readily loses the elements of acetic acid to form 7-methoxy-l,2-dihydronaphthalene which forms a crystalline dimer in the presence of hydrobromic acid. Oxidation of the monomeric substance gives /3-(2-carboxy-5-methoxyphenyl)-propionic acid.