. Annual report on essential oils, synthetic perfumes, &c. Essences and essential oils; Perfumes. CHNH2 CH (I) ^Pinocamphylamine. CH (II) Pinylamine. Ruzicka and Trebler further report on experiments which were partly failures, undertaken to prepare, from pinonic acid (III), the easily-accessible oxidation product of pinene, the homopinocamphoric acid which was not known so far. In this the authors made the following observations: — (1) The ethylpinolate (IV) prepared by catalytic reduction of ethylpinonate yielded with phosphorus pentachloride, in addition to pinocampholenic ester, only l
. Annual report on essential oils, synthetic perfumes, &c. Essences and essential oils; Perfumes. CHNH2 CH (I) ^Pinocamphylamine. CH (II) Pinylamine. Ruzicka and Trebler further report on experiments which were partly failures, undertaken to prepare, from pinonic acid (III), the easily-accessible oxidation product of pinene, the homopinocamphoric acid which was not known so far. In this the authors made the following observations: — (1) The ethylpinolate (IV) prepared by catalytic reduction of ethylpinonate yielded with phosphorus pentachloride, in addition to pinocampholenic ester, only little of the desired chloroester (V). They did not succeed in converting this ester into homopinocamphoric acid. In the preparation of ethylpinonate (b. p. about 100° [one third mm.], semi- carbazone m. p. 136°) it was noticed that pinonic acid was, under certain conditions, easily esterified already by very weak alcoholic hydrochloric acid. (2) In treating the ethylester of pinonic acid cyanohydrin with phosphorus penta- chloride they did not obtain the expected ester of dehydrohomopinocamphoric nitrile acid, but the aliphatic 2-cyano-6-methyl-2:6-heptadiene-5-acetic acid ethylester (VI) which, on saponification, yielded the dicarboxylic acid of constitution (VII). From the latter they obtained, by treatment with acetic acid anhydride in a sealed tube, the intermediary anhydride (VIII) and further the unstable ketone (IX) and carvacrol (X). This reaction represents a new mode of preparing this phenol. By reduction and !) Beteet. ekim. acta 3 (1920), Please note that these images are extracted from scanned page images that may have been digitally enhanced for readability - coloration and appearance of these illustrations may not perfectly resemble the original Schimmel & Co. Miltitz bei Leipzig : Schimmel & Co.
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