— 145 — 



oxide acid C 10 H 16 O 3 (b. p. 140 at 9 mm. pressure), for which he 

 proposes the following formula : — 



CH 2 C H, 



HOOC-C^— -O — )CC 3 H 7 , 



CH 2 CH 2 



A short time ago Semmler 1 ) obtained from sabinene and con- 

 centrated formic acid an alcohol C ]0 H 18 O, which was identical with 

 the alcohol C 10 H 18 O of oil of sweet marjoram ("terpinenol" Wallach, 

 "origano!" Semmler). The formula drawn up at the time is now 

 corrected by Semmler to the following: — 



CH CH 2 

 H 3 C.C^ ^C(OH).C 3 H 7 , 



CH 2 CH 2 



which confirms the formula accepted by Wallach 2 ) for this alcohol. 



With regard to the conversion of sabinene into terpinene com- 

 pounds, see under Terpinene (p. 143). 



Sylvestrene. The process of substituting hydroxyl for chlorine 

 employed by Wallach 3 ) in the case of terpinene dihydrochloride, to 

 which we referred in our last Report, has recently also been applied by 

 this investigator 4 ) to sylvestrene dihydrochloride C 10 H 16 • 2 HC1. 

 10 g. chloride (m. p. J 2°) were shaken with a hot solution of 10 g. 

 caustic potash in 500 cc. water, and the product after 5 hours distilled 

 with steam. The residue contained sylveterpin C 10 H 18 (OH) 2 (m. p. 135 

 to 136 ; Md -[" 2 7>43° m methyl-alcoholic solution), and the distillate, 

 besides some hydrocarbon, sylveterpineol C 10 H 17 OH (b. p. 210 

 to 214 ; d 0,924; n D22 o 1,4822; mol. refr. found 47,53, calculated for 

 C 10 H 17 • OH/ - 47,96), which on shaking with concentrated hydrochloric 

 acid, yielded back sylvestrene dihydrochloride. On oxidation of sylve- 

 terpineol with 1 per cent, solution of potassium permanganate in the cold, 

 the corresponding glycerol C 10 H 17 (OH) 3 of the b. p. 165 (11 mm. 

 pressure) was formed; this is an almost colourless, viscid oil, which 

 did not crystallise. 



The nitrosochloride of sylvestrene passed over, in splitting off 

 hydrogen chloride, into an oxime, which could not be obtained in 

 solid form, but which on boiling with oxalic acid yielded a ketone, 

 whose semicarbazone (m. p. 175 to 1 77°) pointed to the composition 



x ) Berl. Berichte 89 (1906), 4421; Report April 1907, 141. 



2 ) Ibidem 40 (1907), 596; Report April 1907, 137. 



3 ) Liebig's Annalen 350 (1906), 153; Report April 1907, 135. 



4 ) Nachr. K. Ges. Wiss. Gottingen 1907, Meeting of 8. June. 



