— i3 2 — 



d^jJ- 0,8729; n D2i,i° M99 1 ; b - P- 86 t0 8 7>5° ( l6 mm. pressure), 

 1 9 8° (732 mm. pressure). In an analogous manner is also formed 

 2-ethyl-p-cymene from 2-ethyl-zf 2 , 6, 8 (9)- m enthatriene. 2-Ethylcarveol: 

 d^- 0,9302; Md2io+3M7 ; n D2i° i,4879; b. p. 118,5 to 119,5° 



1 QO 



(14 mm. pressure). 2-Ethyl-Zi2, 6, 8(9)- m enthatriene: d-^- 0,8859; [«] D1 8o 

 -4-86,19°; n D18 o 1,5041; b.p. iooto 101° (13,5 mm. pressure). 2-Ethyl-p- 



911° 



cymene: d-^- 0,8665; n D2i,i° iA9^5l b - P- io 3° (19 mm. pressure). 

 This conversion into the benzene hydrocarbon is most easily accomplished 

 with 2 -phenyl carveol; in this case, even the 2 -phenyl menthatriene 

 was not obtained in the pure state. 2-Phenyl-carveol: d-^- 1,0156; 

 Mdi5,i° +81,42°; n pi5,io 1,5562. The crude oil boiled at 145 to 168° 

 (12 mm. pressure), the bulk at 159 to 160°. 2-Phenyl-Zl2, 6, 8(9)- 

 menthatriene: highest rotation observed -|- 1 10,2° (13,8°); d-^- 0,9882 ; 

 n Di3,8° i,5 6 3 T ; b - P- I 5 2 to ^S ( x 3 m m. pressure). 2-Phenyl-p- 

 cymene: d^ 0,9822; « D150 +0°; n D13j80 1,5670; b.p. 153 to 154° 

 (14 mm. pressure). 



V. J. Nikitine 1 ) has produced some new terpene alcohols 

 derived from carvone and dihydrocarvone respectively. If, according 

 to v. B a e y e r , alcoholic potash is allowed to act on the hydro- 

 bromide of dihydrocarvone in a freezing mixture, carone is for- 

 med, and from the latter, by treatment with sodium in ethereal 

 solution, an alcohol C 10 H 20 O (b.p. 103° [12 mm. pressure], n D 1,4651, 

 d^o" 0,9086; [«] D 24,36°), which can be converted into caromenthane. 

 By the action of methylmagnesium iodide there is formed from carvone 

 an alcohol C u H 20 O, b. p. 99 to 101° (13 mm. pressure); and when 

 dihydrocarvone is reduced with sodium and alcohol, there results an 

 alcohol C 10 H 18 O (b.p. 107 to 108° [17 to 18 mm. pressure], 220° 

 [ord. pressure], di 9}5 o 0,9224, n D 1,4773, [a] D -|_2 2,9°), which is there- 

 fore, according to its constants, not identical with Wallach's dihydro- 

 carveol. 



If molecular quantities of hydrocyanic acid and carvone are al- 

 lowed to act on each other 2 ), there is formed cyanodihydrocarvone 

 (m. p. 93,5 to 94,5°; Md + I3>5° in alcoholic solution): 



/CO C H 2\ /^^ H 2 



CH 3 .CH< >CH.Cf 



\CH(CN).CH,/ X CH 8 



x ) Journ. russ. phys.-chem. Ges. 36, 780. 

 2 ) Proceed. Chem. Soc. 20 (1904), 54. 



