— 193 — 



purified by distillation with steam, in the course of which process tetra- 

 hydro-p-acetyltoluene oxime passes over. The acetyloxime which remains 

 behind in the flask can be crystallised by adding ligroin. When re- 

 crystallised from ligroin and benzene it melts at 111 to 112°, on dry hea- 

 ting it gives off acetic acid and forms tetrahydro-p-acetyltoluene oxime. 

 It is remarkable that the two nitrosochlorides described above yield the 

 same acetyloxime. 



When 5°/o sulphuric acid is poured over the acetyl oxime and distil- 

 lation is proceeded with in a strong current of steam, hydroxy-4-hexa- 

 hydro-p-acetyltoluene 



TH / \/ 0H 



results: m. p. 21 to 22°, b. p. 223 to 224°. This compound volatilises 

 readily with steam, and when exposed to air forms a semicarbazone 

 m. p. 219 to 220°, and an oxime, m. p. 128°. When the acetyloxime or 

 the hydroxyketone is heated with 20% sulphuric acid the result is tetra- 

 hydro-p-acetyltoluene. 



The treatment of hydroxy-4-hexahydro-p-acetyltoluene with magnesium 

 methyliodide gives rise to a mixture of stereo-isomeric glycols, one of 

 which, (m. p. 97 to 98; b. p. 245°) can be isolated. Oxidation with aqueous 

 permanganate of potassium yields p-methyl-c?/cfohexanone , showing the 

 glycol melting at 97 to 98° to be 4,8-menthanediol (4,8-terpine) 



CH '-< X,OH)< CH * 



A comparison with the already known terpines shows that the closer 

 mutual approach of the hydroxyls in the terpine molecule increases the 

 volatility; 4,8-terpine volatilises readily; 1,4-terpine with difficulty, and 

 1,8-terpine is not volatile with steam. 



Cryptomeriol. In our last Report we mentioned Kimura's 1 ) discovery 

 in oil of Cryptomeria japonica of a liquid sesquiterpene alcohol, to which he 

 had given the name of cryptomeriol and which had given rise, when purified 

 by way of its xanthogene compound, to a crystalline alcohol called by 

 the author isocryptomeriol. Kimura also indicated that he was engaged 

 in investigating whether it was possible to convert the sesquiterpene alco- 

 hols santalol and cedrol (cedar-camphor), from the liquid into the crys- 

 talline form by such agents as alkali metals or steam, or by formation of the 

 xanthogenic acid esters. , . t 1 c 



This examination, which has lately Jbeqi cajried out 2 ), has given very 

 favourable results in the case of cedar opd oil free from terpenes and 



x ) Berichte d. deutsch. pharm. Ges. 19 (1909),, oart April 1910, 45. 



2 ) Berichte d. deutsch. pharm. Ges. 20 (1910), 2^3." 



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