> alt i ’ 
° the aforesaid ieiteaael with the ‘ethyl group in the ‘side- chain. The 
erpineo! prepared from ae nopinol forms a phenylurethane of the m. p. 92 to 
ve i | CH, 
~ mS ne 
The corresponding terpine HsCo- eS Oy hey Cx. OR, dihydroxy-1, cae 1-iso- 
ad ~ ess se Noh? Hs 
1L4-cyelohexane, melts at 75 to 76°. oe 
or degrading unsaturated hexacyclic compounds down to benzene hivdeocarbabe: 
as found to be convenient to treat the unsaturated alcohols with one double bond, 
eo difficult to Aa AS From pe p-cymene, from sylveterpineol 
y mene), from ‘the afore- described 4'-methyl- 1- Ste Or cet Sey one xene Dyke 
se ood “solubility in acetone of most nitrosochlorides and by Aap nOS pyridine for 
SI itting off hydrogen chloride. By this method, a very satisfactory yield of carvoxime 
resul , when 7 g. limonene nitrosochloride, 3 c.c. pyridine, and 6c.c. acetone are 
med from 10 to 15 minutes in a boiling water-bath and the cleat warm solution 
treated with some water. — \ ‘3 
"ig In course of the investigation of the terpineol nitrosochlorides it has been foukid 
that the manner in which hydrogen chloride is split. off may be markedly influenced — 
act ording to the reagent used for abstracting the hydrogen chloride. If «-terpineol — 
1 trosochloride (Il) is treated in the manner described above for limdnene nitroso- — 
ot loride, with pytidine in acetone solution, the result is an unsaturated oxime of the 
. p. 134° (II), formerly termed hydroxy dihydro carvoxime, but more correctly it — 
uld be named hydroxy-8-carvotanacetone oxime or A®- -hydroxy-8-menthenone-2-oxime. 
atment with sodium acetate, however, leads to an entirely different result. When 
NOH sed Sale Sena >A ORY ig 
eee P. BR eg at Cg | : 
oc <Cl OH ES He Lon 
es fo ; | 
me) po se yay cH, Ko oi Nor, 
ees oinesl nitrosochloride. ' oe ) (11) A®-Hydroxy-8-menthenone-2-oxime. 
: kating a-terpineol _nitroso- rot | NOH 
chi oride with its own weight of — 3 | we I ic CH, 
1 acetate, then adding the five-fold weight of HsC— Ce 
glac al acetic acid and warming until reaction has | es | 
A, the chilled mixture yields, after addition of | O 
rand after neutralization with alkali, a Seba ae (Ill) Saturated oxime oxide. 
4 Haworth, Perkin and Wallach, Liebig’ s Annalen 399 ad 166; Report October 1913, 136. — %) Liebig’s 
Annal pas en 
