Bot ialt shit 
88 | REPORT OF SCHIMMEL & Co. | OCTOBER 1914/ ety 1915. 
mate, 
off water through potassium pyrosulphate, this alcohol is converted into benzo-A2940. i 
nor-p-menthene (VI), which smells like cedrene and shows great indifference towards — a 
potassium permanganate; b. p. 259 to 261° (745 mm.) No nitroso compound was ob- 
tained. When heating the hydrocarbon with sodium alcoholate in a sealed tube, it is 
converted into benzo-4’°“-nor-p-menthene. In the same way benzo-A?-nor-p-menthen- 
10-01 (VII), m. p. 101 to 102°, forms from ethyl 41-dihydro-e-naphthoate. It has an 
odour like. naphthalene. By splitting off water by means of potassium pyrosulphate, 
benzo-A*!0%-nor-p-menthadiene (VIII) was obtained, b. p. 255 to 256°. After reduction 
it affords benzo-4!°-nor-p-menthene (see above). 
CHe CH CH 
CH-CH, : Reichs | 
AS en Aen Sen Aen 
VX jo A jem \ A th XR 
CH : 
CH: CO.H CBr : CO.C.H; C : CO, Cy Hs 
CH (I) (II) (IV) 
wv. Tetrahydro- Ethyl a-bromotetrahydro- Ethyl 
fac -CHs a-naphthoic acid. a-naphthoate. A'-dihydro-a-naphthoate. 
(1) Benzo-p-menthane. 
CH, CHe CH CH, | 
eon 7 eae (Neon (a 
ee  Aec Nee \AN\G NG 
CH CH C C 
C-OH C C-OH C 
ix aX JN IN 
H;C CHs H;C CH. H3;C CHs H;C CH, 
(V) Benzo- (VI) Benzo- (VII) Benzo- (VII) Benzo- 
nor-p-menthan-10-ol. A(D-nor-p-menthene. A38-nor-p-menthen-10-ol. A® 0GD-nor-p-menthadiene. 
Furthermore the preparation of «-naphthyldimethyl carbinol and «-isopropeny]- 
naphthalene is described. 
The relationship of p-benzo-p-menthane to the sesquiterpenes is to be seen in the 
following scheme:— 
HC CH-CHs CH, C-CHs 
Nee 4No/ ~ cry Hec-HC” NE“ \\ cH 
| 
re yay Ae ae 4 CH, me ANZ CH, 
CH CH 
CH, 
Naphthalene. CH a 
De 7 Ye 
Benzo-p-menthane. a-Selinene 4), 
Styrene. The fact that pure styrene does not change spontaneously into meta- 
styrene ought, according to H. Stobbe’), to lead to the supposition that an equilibrium 
would finally result in such homogeneous systems, 2. e. that every polymerization was 
1) Comp. Report April 1918, 138. — 7) Berl. Berichte 47 (1914), 2701. 
