Commercial notes and scientific information. 33 



constants point to «-pinene. The nitrosochloride of the fractions in question had 

 m. p. 103°, the corresponding benzylamine base melted at 123 to 124°. The fraction 

 therefore contained d-«-pinene. 



A fraction possessing the b. p. of camphene gave the following constants: 

 di 50 0,8639, « D -f-5°37\ On hydration with glacial acetic-sulphuric acid it afforded a 

 large proportion of ^soborneol, but in spite of repeated purifications from light petroleum 

 the m. p. of the last-named body remained as low as about 208°. Small quantities of 

 /?-pinene were found in a fraction possessing the following physical properties: b. p. 

 163 to 167?, d 15 o 0,8607, « D — 0°20', n D20O 1,47102. When treated with permanganate 

 and alkali it yielded in the form of an oxidation-product the characteristic leaflets of 

 sodium nopinate, from which nopinic acid, m. p. 124 to 126°, was obtained. Oxidation 

 of the sodium salt with permanganate in acid solution afforded nopinone, of which 

 the semicarbazone had m. p. 186 to 188°. 



The oil contained neither ^-cymene nor phellandrene. The identification of the 

 first-named hydrocarbon was attempted from fractions boiling between 170 and 175° 

 and 175 and 178° respectively, by oxidation with permanganate. Fractions of the same 

 b. p. were tested for phellandrene, but they neither yielded the nitrite nor the oxidation- 

 products characteristic of phellandrene. On the other hand, dipentene was readily 

 identified in fractions with b. p. 175 to 178° (d 15 o 0,8572; « D — 6°36'). Bromination in 

 glacial acetic acid solution gave rise to the tetrabromide, m. p. 125 to 126°. 



d-Borneol was found to occur in the following mixture, which distilled over between 

 55 and 85° (5 mm.). When fractionated once more it congealed in the condenser. 

 Filtered by suction the crude product, when tested for camphor with semicarbazide, 

 proved to be camphor-free. The borneol, after being purified by recrystallisation from 

 light petroleum, indicated the desired m. p., viz., 204°. Its chloroform solution was 

 dextrorotatory. 



With the object of setting free the borneol from the higher boiling fractions of 

 the oil and from the mother-liquors, these latter were benzoylated with benzoylchloride, 

 with the aid of pyridine. The oil which was driven off in the steam-current by this 

 manipulation, and which was not esterified, proved to consist substantially of l-a- 

 terpineol, m. p. 35°. A fraction gave the following constants: di 5 o 0,9379, « D — 8°2\ 

 When inoculated under cooling it solidified completely. The resulting phenylurethane 

 had m. p. 112°. After saponification of the residue of steam-distillation no alcohols 

 other than borneol were discovered. In view of the fact that during the fractionation 

 of Borneo-camphor oil a great deal of resin was left behind in the residue, we con- 

 sidered it advisable to rectify a little of the oil by steam-distillation in order to test 

 the oil -fractions with the highest b. p. Those oil -fractions which entered into con- 

 sideration for testing for safrol and other bodies of high b. p. were further resolved, 

 but it was then shown that no constituents of the odour and b. p. of safrol, 230 to 235° 

 were contained in them. The highest boiling fractions b. p. 102 to 112° (4 to 5 mm.), 

 consisted only of sesquiterpenes. None of them, when warmed, reacted with strong 

 formic acid; hence no sesquiterpene alcohols were present. One fraction was found 

 to possess the following constants: b. p. 102° (4 to 5 mm), 256 to 260° (ord. press.), 

 di 50 0,9200, a D — 137° 12', n D20 o 1,50111. From the analysis and from treatment with 

 sodium it was evident that the fraction contained no oxygenated constituents. 

 0,1968 subst: 0,6371 gr. C0 2 , 0,2073 gr. H 2 0. 

 Found Calc. for Ci 5 H 2 4 



C 88,29 p. c. 88,23 p. c. 



H 11,70 p.c. 11,76 p.c. 



