. Annual report on essential oils, synthetic perfumes, &c. Essences and essential oils; Perfumes. CHS I HC HC2 C(CH3)2 CH CHCOOH COOH CH2. COOH HC H2C (II) Glycidic dicarboxylic acid from pinonic acid. CH3 I CH COOH COC C(CH3)2 CH3 I CH CH2 HC <^ s-i. ^C(CH3)2 H2C "\^ 'l0§ CH (III) Homopinocamphor- aldehydic acid. CO CH2 CH (IV) Homopinocamphoric acid. CH (V) Pinocamphone. by condensation of the diethyl ester of the (IV), in xylene solution, with sodium. The ketonic acid ester formed primarily was saponified, with formation of pinocamphone, by boiling with a 15 per cent, hydrochlor
. Annual report on essential oils, synthetic perfumes, &c. Essences and essential oils; Perfumes. CHS I HC HC2 C(CH3)2 CH CHCOOH COOH CH2. COOH HC H2C (II) Glycidic dicarboxylic acid from pinonic acid. CH3 I CH COOH COC C(CH3)2 CH3 I CH CH2 HC <^ s-i. ^C(CH3)2 H2C "\^ 'l0§ CH (III) Homopinocamphor- aldehydic acid. CO CH2 CH (IV) Homopinocamphoric acid. CH (V) Pinocamphone. by condensation of the diethyl ester of the (IV), in xylene solution, with sodium. The ketonic acid ester formed primarily was saponified, with formation of pinocamphone, by boiling with a 15 per cent, hydrochloric acid. The semicarbazone and the oxime of the dj-pinocamphone thus obtained were identical (as was proved by the melting- point of the pure substance and of the mixture) with the corresponding preparations of Wallach3) resulting from a ^/-pinocamphone from nitrosopinene by treatment with zinc and acetic acid. Since pinocamphone may be transformed into pinylamine and «-pinene by means of the reactions described already by the authors4), an uninterrupted way is given for the partial synthesis of a-pinene from «-pinonic acid. Hitherto it has been generally taken for granted that on addition of dry hydrogen chloride to pinene always pinene hydrochloride = bornyl chloride (I) is formed. O. Aschan5) proved this assumption to be incorrect, as the isomeric liquid, tertiary pinene hydrochloride is formed in this reaction. This compound, stable only at a temperature below —10°, partly splits off hydrogen chloride on treatment with aniline and yields pinene rotating in the same sense as the starting material. When the tertiary pinene hydrochloride is removed from the freezing mixture, it rises in temperature up !) Compt. rend. 139 (1904), 1214. — *) Cf. Bericht (Germ, ed.) 1921, 106. Chem. Zentralbl. 1921, III. 629. *) Liebig's Annalen 317 (1901), 27. — J) Ibidem 304.(1898), 287. - B) Vetenskaps Akad. Forhand. 67, part A. 1914, No. 1. As per. Please note that these images are
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