134 REPORT OF SCHIMMEL & Co. APRIL 1914. 
calls it, affords a chromate with m.p.92°; [¢]Lirea + 30,0°. From the above it is 
evident that cedrol and ledol are tertiary aleanite, Patchouly camphor also gives a 
stable chromate, but guajol does not. | 
We fail to find in the interesting paper of Wienhaus any reference to a compound ~ 
of chromic acid and maali alcohol. It is true that the last-named body was not 
identified by us as a chromic ester at the time, but it is doubtless an organic chromate’). 
In the same investigation we referred to the chromic acid compounds of patchouly 
alcohol (m. p. 52 to 53°), of sesquiterpene alcohol (globulol)*) from the oil of 
EHucalyptus Globulus (m. p. 78°), and of ledum camphor. 
Citronellol. The investigations of Tiemann and Schmidt), Semmler*), Harries 
and Himmelmann®) on the one side, and those of Harries and Roeder®) and of Harries 
and Schauwecker’) on the other, have resulted in the acceptance of two: different 
chemical formulz for natural citronellal, namely 
CH;-C-CH2-CH2:CH,-CH-CHs-CHO and CH;-C:CH-CH2-CH:-CH-CH:-CHO 
CH, CH; CHs CHs . 
Limonene form. Terpinolene form. 5 
ae = 
From the research of H. Rupe and A. Jager*) which is referred to on p. 136 of the 
present Report it is also evident that citronellal constitutes a mixture of two chemi- 
cally different bodies of the chemical structure set forth above. On the other hand, 
chemists are still greatly at variance on the question whether, as held by Tiemann 
and Schmidt®) and by Schimmel 8 Co.*°). /-citronellol of geranium oil and rose oil 
and ordinary d-citronellol (from citronellal) represent merely two optically different 
modifications of one and the same alcohol, or whether Barbier and Bouveault*’), 
Bouveault and Gourmand *”), and Barbier and Léser?*) are correct in assuming the two 
bodies to be alcohols of different constitution, namely rhodinol and citronellol. In 
continuation of previous investigations, P. Barbier and R. Locquin**) in a recent publi- 
cation attempt to bring further proof to show that rhodinol and citronellol are alcohols 
of different constitution. 
In this publication the authors mention a number of experiments in which citconetal 
has been converted into rhodinol. Taking as their starting point the acetic ester of 
Ordinary d-citronellol and /-citronellol (rhodinol from oil of geranium or rose), the 
authors attach hydrogen. chloride or hydrobfomic acid to the double bond, and, as is 
to be expected, they obtain the same additive product according to the following 
equation: — 
CH; -C-CHe- CHa: CH, -CH-CH2:CH,0H 
> & 
; 
; 
| 
nen tk co -+-HX = CH,-CX-CH,-CH,-CH,-CH Chacon 
CH; CHs 
CH,;-C : CH-CH,: CH.: CH: CH2: CH, OH 
CH; CHs 
Rhodinol. 
1) Report November 1908, 139. — 2%) Report April 1904, 51; October 1918, 59. — %) Berl. Berichte 29 
(1896), 903; Report October 1896, 88; Beri. Berichte 80 (1897), 22; Report April 1897, 58. — +) Berl. Berichte 26 
(1893), 2257. — 5) Berl. Berichte 41 (1908), 2187; Report November 1908, 185. — *) Berl. Berichte 82 (1899), 
3367. — 7) Berl. Berichte 84 (1901), 1498, 2981; Report October 1901, 70; April 1902, 90. — %) Liebigs Annalen — 
402 (1914), 149. — %) loc. cit. — 1) Report October 1904, 119. — 1) Compt. rend. 122 (1896), 737, 793; 
Bull. Soc. chim. Ill. 28 (1900), 458; Report October 1900, 76. — 1) Compt. rend. 188 (1904), 1699; Report October — 
1904, 118. — 18) Compt. rend. 124 (1897), 1308; Report October 1897, 66. — 1) Compt. rend. 157 (1913), 1114. 
