— 145 — 



the CHO-group, possess one or more labile hydrogen atoms. In col- 

 laboration with E. Schossberger 1 ) the author has continued these researches 

 by investigating the action of acetic anhydride upon citral. The authors 

 where able to show that in this reaction one double bond of citral migrates 

 into the conjugated position. Enol-citral acetate boils at 118 to 126° 

 (10 mm.); d 20 o 0,9420; n D 1,5010; mol. refr. calc. as ester Ci 2 Hi 8 2 Al 58,02, 

 found 60,60. Citral diacetate had been formed as a by-product. When 

 enol-citral diacetate was reduced with sodium amalgam and methylalcohol 

 it gave rise to an alcohol which proved to be different from geraniol and 

 nerol, and to which the name of isogeraniol was given. This new alcohol 

 possessed the following constants: b. p. 102 to 103° (9 mm.), d 2 oo 0,8787, 

 n D 1,47325. Its diphenylurethane had m. p. 73°. 

 phenylurethane was obtainable in the crystalline 

 believe that the reaction proceeds as follows: — 



No tetrabromide or 

 form. The authors 



H 3 C 



XH 2 



CH 2 



CH 

 (OH)HCn Ns 



2 





CH 



z 



OHC| >CH 2 



CH 2 — > 



(OH)H 2 C 



NcH 2 



HcL JcH 2 

 C 



c 



CH 



H 2 C 



\/ CH 



c 



CH 3 



CH 3 



/ CH 8 



Citral. 



Enoiic fori 



n I. 



/ 



'/'■ Jsogeraniol I. 



1 



H 3 Q XH 2 



H 3 C X 



y 



H 3 C //^ <i 



CH 2 

 (HO)HCn NcH 2 — 



CH 2 



CH 2 



-> (HO)HCm \cH 2 — ^ 



(OH)H 2 C, ^ 



CH 2 



Clk JCH 2 

 C 



HCni, Jch 2 

 c 



H 2 Cl v 



c 



CH 2 



CH 3 



possibly primarily. 



CH 



Enolic forr 



2 



n II. 



Isoi 



CH 



jeranio 



2 



1 II. 



In our last Report 2 ) we referred to a triphenyl methane derivative which 

 had been obtained by Szeki by treating asarylic aldehyde with hydrochloric 

 acid of 25°/o. The same author 3 ) has also obtained a series of other 



!) Berl. Berichte 44 (1911), 991. 



2 ) Comp. Report April 1911, 180. 



3 ) Berl. Berichte 44 (1911), 1476. 



10 



