— 142 — 



Isoborneol. Semmler and E. W. Mayer 1 ) have ascertained that 

 camphene, when boiled with formic acid in a reflux-condenser, is con- 

 verted quantitatively into isobornyl formate. 20 g. Camphene yielded 24 g. 

 formate. The ester gave the following constants: b. p. 91 to 93° (11 mm.), 

 d 20 o 1,005, n D 1,4726. 



Thujyl Alcohol. Paolini 2 ) reports on experiments in the prepara- 

 tion in the pure form of one of the isomeric thujyl alcohols. Several in- 

 vestigators have obtained isomeric thujyl alcohols by reducing the several 

 thu jones according to various methods, as well as by reducing sabinol, 

 but nothing has been reported concerning the separation of these alcohols. 

 When the ketone of thuja oil or of tansy oil (which, according to Wallach, 

 is a mixture of a large proportion of «- with a small proportion of /?-thujone 

 and vice versa), is reduced, the result is a mixture of two isomeric alcohols 

 corresponding to the two ketones, not taking in account that owing 

 to the appearance of a new asymmetric carbon-atom during the process 

 of reduction, a fresh source of isomerism has been opened up. The 

 rotation ascertained by the several investigators varies: Kondakoff gives 

 Md + 45°57\ Tchugaeff, [«] D + 69 49', which shows that the alcohols 

 obtained in the process of reduction are not absolutely identical, a fact 

 which points to the presence of an isomeric alcohol which is optically 

 either lasvorotatory or, — but more faintly — dextrorotatory. Semmler has 

 observed, moreover, that when "thujyl alcohol" is oxidised, the ketone which 

 it yields is not quite the same as the fundamental ketone, its rotatory 

 power being less than that of latter, and Tchugaeff s observations on the 

 formation of two thujenes from tanacetyl alcohol by his xanthogenate- 

 method have confirmed the conclusion that the bodies in question are 

 isomeric alcohols. Paolini has tried, by means of acid phthalic ester, to 

 split up the tanacetyl alcohol which is obtained from /?-thujone by reducing 

 it with sodium and alcohol. The crude phthalate appeared as a semi- 

 liquid, sticky mass, very readily soluble in most of the organic solvents, 

 and capable of purification by repeated solution in benzene and pre- 

 cipitation with an abundance of light petroleum. Final recrystallisation 

 from light petroleum afforded an ester acid which might be regarded as 

 a uniform body, as the m. p. (120°) showed no further increase. The 

 rotation of the ester acid, of which the silver-, the calcium-, and the 

 strychnine-salts were prepared and analysed, was in a solution of 1,0956 g. 

 of the substance in 100 cc. absolute alcohol +2°0' in a 2 dm.-tube; which 

 gives [a] D + ^l°27\ When the ester acid was saponified during half 

 an hour in a water bath, it yielded the free alcohol, constants: b. p. 206°, 

 d 0,9229, « D + 105°50', n D16 o 1,4625. 



*) Berl. Berichte 44 (1911), 2012. 



2 ) Rendiconti della R. Accademia dei Lincei. Vol.20, 1 st Semester, No. 10, p. 765. Meeting 

 of 21 8t May 1911. From a reprint kindly sent to us. 





