— 166 — 



from turpentine oil. It has the same composition as the latter, but 

 is somewhat, better soluble and is dextrorotatory, whereas the one 

 from turpentine oil is laevorotatory. The acid liberated from the salt 

 has the m. p. 154 to 155 (from benzene), and is stable towards hot 

 12 per cent, sulphuric acid, contrary to nopinic acid which yields 

 hydrocuminic acid. It is also a hydroxy acid, as is shown by the oxid- 

 ation, which was carried out as in the case of nopinic acid. But 

 the ketone C 9 H 14 differs from nopinone. It is solid (m. p. about 6o°) 

 and possesses an odour reminding of camphenilone and fencho- 

 camphorone. M. p. of the semicarbazone 206 to 207 . 



The synthetic terpene could be converted with glacial acetic and 

 sulphuric acids, according to Bertram and W a 1 b a u m , into the crystallised 

 alcohol C 10 H 18 O (m. p. 62 to 63 ; b. p. 202 to 204 ) which has a 

 camphor-like odour, and which on oxidation with chromic acid yielded 

 a ketone C 10 H 16 O solidifying at a very low temperature, whose semicar- 

 bazone melts at 220 to 22 1°. This behaviour reminds strongly of 

 the hydrocarbons obtained by Aschan 1 ) from the liquid hydrochlorides 

 from turpentine oil. 



From the observations communicated, Wallach draws the conclusion 

 that the synthetic hydrocarbon from nopinone differs physically and 

 probably also chemically from the nopinene (/?-pinene) of turpentine 

 oil which supplied the nopinone used for the synthesis. For this 

 reason it is believed that in the formation of the artificial terpene 

 from nopinone, a configuration-displacement occurs. 



Methylcyclohexanone. W. Markownikow and W. Smirnow 2 ) 

 have worked on some derivatives of /5-methylcyclohexanone, with the 

 view of arriving at a suitable crude material for the production of 

 hexahydro-m-toluylic acid. The most suitable for this purpose appeared 

 to be the hydroxy acid corresponding to jff-methylcyclohexanone, which 

 could be produced in the most practical manner by the following 

 method. The cyanohydrin of ^-methylcyclohexanone (m. p. 63 to 64 ) 

 is dissolved with cooling ( — 15 ) in 3 parts concentrated sulphuric 

 acid; after 24 hours' standing this is diluted with water, and in this 

 manner an amide C 8 H 15 2 N (m. p. 120 to 12 1°) is obtained, from 

 which by heating with dilute sulphuric acid (d 1,32) the corresponding 

 hydroxy acid C 8 H 14 3 (b. p. 163 to 166 [12 mm. pressure], 260 to 270 

 with partial decomposition [733 mm. pressure]), is readily formed. 

 This acid, however, consists apparently of two isomerides, for on 

 heating with aniline (molecular quantities) there are obtained two 

 sevorotatory anilides of the m. p. 90 to 91 and 118,5 to II 9>5° 



x ) Comp. the present Report, p. 136. 



2 ) Journ. Russ. phys.-chem. Soc. 39 (1907), 1. Accord, to Chem. Zentralbl. 1907, 

 I. 1407. 



