— *4i — 



m. p. 53 to 54 as certainly identical with his own of the m. p. 51 to 52 . 

 The slight difference might be explained by a difference in the manner 

 of determining the melting point. According to Wallach's 1 ) exam- 

 inations, the dihydrochloride is not formed at all if moisture is care- 

 fully excluded, but only a monohydrochloride, which therefore is best 

 obtained in a solution of carbon disulphide. It has the following 

 properties: b. p. 87 to 92 (12 mm. pressure); d 0,982; n D20O 1,4842. 

 It could not be obtained in the solid form, and contrary to limonene 

 monochloride, formed no difficultly soluble nitrosate, but a nitroso- 

 chloride. By adding hydrogen chloride it is converted in the dichloride 

 of the m. p. 5 2 . In a study dealing with the formula of the mono- 

 chloride, Wallach comes to the conclusion that he is unable to confirm 

 Semmler's proposition that the double linking of the pseudo-form 



adds hydrohalogen with much greater difficulty, than the ortho-form 



CH -/ \ 



When treating sabinene with formic acid at a highly reduced temp- 

 erature, and saponifying the resulting formiate, Semmler 2 ) obtained 

 an alcohol C 10 H 18 O (b. p. 93 to 96 , at 1 1 mm. pressure; d2o° 0,926; 

 n D 1,48033; «d -J- 14 ), which by the action of glacial acetic acid 

 and hydrochloric acid yielded a dichloride of the m. p. 51 to 5 2°. 

 Semmler considers this provisionally as identical with the terpinene 

 dihydrochloride of Wallach, and compares his alcohol with the one 

 discovered by Wallach in oil of sweet marjoram, for which Semmler 

 proposes the name origanol. The synthetic alcohol, when oxidised 

 with potassium permanganate, yields a glycerol which Wallach ob- 

 tained from the alcohol of oil of sweet marjoram. If the formiate of 

 the alcohol from sabinene is heated with quinoline to 230 , there 

 results a terpene C 10 H 16 (b. p. 174 to 177 ); d 20 o 0,839; n v l A79> 

 «d~|-4 I2 / ) which gives a feeble terpinene reaction. When treating 

 the alcohol with phosphorus pentachloride, with the application of 

 heat, a terpene is obtained which gives a powerful terpinene reaction. 

 A urethane or any ester of the alcohol could not be obtained. 



The treatment of this alcohol with glacial acetic acid and hydrogen 

 chloride, which Semmler carried out for the determination of its 

 constitution gives Wallach 3 ) an opportunity of criticising the above- 

 mentioned view of Semmler, that the addition products of hydrogen 



x ) Berl. Berichte 40 (1907), 588. 

 *) Berl. Berichte 39 (1906), 4421. 

 3 ) Berl. Berichte 40 (1907), 595. 



