bes ai: 7a a Sa aac ic 
ern ee tect} mye Fave : 
ee tas Ua cht pas Pd eae a Ys CO car aa ae BS 
Apa Set on ES AES »: ae ene ie tue vee 121 
a a e soar ise eat ep aie Taney 
to ol btain different miycal by: Shtdne’ frome carvone and by altering the con- 
1s of their formation. However, this could not be realized, probably for the 
as on that carvone itself contains only one asymmetric carbon atom. 
_ On ‘comparing dihydropinol hydrate with other glycols of isomeric structure the 
ywing facts were found: Menthane-1,4-diol, m.p. 137 to 138°, obtainable by various 
i thods, is entirely different from i-dihydropinol hydrate. A second menthane-1,4-diol 
had been obtained from ascaridol'). Dihydropinol hydrate was furthermore compared 
with the menthane-2,4-diol obtainable from sabinene glycol. On treating sabinol with 
a ted sulphuric acid there results a glycol the structure of which, it is true, is not 
quite elucidated’), and which on reduction according to Paal yields a glycol 
P | obably identical with menthane-2,4-diol. It could not be recrystallized, melts, after 
pressing, at 93 to 94°, and is certainly not identical with dihydropinol hydrate. 
a “With the object of studying the behaviour of the unsaturated glycol from sabinene 
gly col, Wallach treated it with oxalic acid in order to abstract water therefrom. A 
mixture was obtained containing a hydrocarbon giving the reaction for terpinene, and 
h unsaturated alcohol which by its constants and its derivatives proved to be carvenol, 
4*-menthenol-2, since by oxidation carvenone, by reduction tetrahydrocarveol were 
3 ained. In this alcohol there may be contained 4*®-menthenol-2, which may be 
fort ed from menthane-2,4-diol by dehydration equally well as carvenol. 
4 On decomposing i-dihydropinol hydrate with oxalic acid a mixture resulted, the 
p aa constituent of which was an oxide of cineole-like smell, besides dihydro- — 
carveol. Rupe*) has proved years ago that menthane-2, 8-diol could be split up in the 
sa ne manner by aid of acids. 
aa 
$3 
Dprsitrofenchotene alcohol. — Mahe wants Bee, Wallach‘) described the hetiucniod: with 
odium and alcohol, of «-fenchonitrile, when fencholenamine results, and additionally 
h od oxyfencholenamine, on using anhydrous alcohol. When fencholenamine is brought 
t ) react with nitrous acid, there results not the unsaturated alcohol, as was to be 
s ected, but, with molecular rearrangement, a tertiary alcohol. This alcohol wes 
o iced by Wallach®) to the saturated body dihydrofencholene alcohol by aid of Paal’s 
| met od and adding acetone. It had a pleasant smell. On reducing «-fenchonitrile 
with sodium there was obtained, in addition to fencholenamine, its hydrate, a viscid 
liquid, b. p. 134° (15 mm.) which could not be brought to solidify. On treatment with 
. ium nitrite and glacial acetic acid, the hydroxy base yielded fencholenalcohol and 
ag glycol CioHis(OH)2, m. p. 103 to 104°. 
CH, CH, ee 
7 ; | yor 
a CH, Coates Hs 77 ; 
— ee P ee | CH, 
.. +-c€ | | econ. -NH, cole CKCHi NH, 
a - a-Fenchonitrile. er Fencholenamine. CH, ‘Hydroxy- CH3. 
ar ; fencholenamine. 
~ Isoamylearvenol. —On p. 21 of our Report 1917 we! described inter alia the ses- — 
guiterpene alcohol isoamyldihydrocarveol abtained by Semmler and Oelsner as by- 
product of isoamyldihydrocarvone. As we gather from a new paper of F. W. Semmler, 
4) Liebig’s Annalen 392 (1912), 61; Report October 1912, 114. — +) Liebig’s Annalen 860 (1908), 100; 
Hepor April 1908, 166. — #*) Berichte 38 (1905), 1723. — *) Liebig’s Annalen 268 (1891), 138; 269 (1891), 369. 
=) Ibidem, 414 (1917), 227 
