Amjuiy,ri8i?arm-}  The  Violet  Perfume.  351 
C(CH3)2CO 
xCO  NH 
previously  prepared  by  Gabriel. 
Synthetical  Researches. — The  authors  made  a  series  of  synthetical 
researches  in  order  to  throw  further  light  on  the  constitution  of 
Irone  and  Irene.  They  started  with  geranial  (called  by  Dodge, 
citriodor-aldehyde),  also  called  citral.  This  has  been  shown  by 
Semmler  to  have  the  constitution 
1        23  45678 
CH3-CH-CH9-CH:CH-C:CH-COH 
I  I 
CH3  CH3 
for  when  treated  with  KHS04  it  yields  cymol  and  with  HI,  (p)  iso- 
propylmethylbenzol  (cymol)  much  easier.  This  geranial  is  con- 
densed with  acetone  and  yields  Pseudionone  as  follows :  (Erchmann, 
p.  173).  In  a  stoppered  flask  Cij4  L)  are  added  65  cc.  acetone;  50 
cc.  geranial,  and  1  L  of  cold  saturated  baryta  water.  Shake  this 
mixture  thoroughly  and  allow  to  stand  for  several  days.  The  pro- 
ducts of  the  reaction  are  removed  with  ether,  the  ether  evaporated 
and  the  residue  distilled  under  diminished  pressure.  That  which 
distils  at  I38°-I55°  (12  mm)  is  preserved.  From  this  product  the 
unattacked  citral,  acetone  and  other  condensation  products  are 
removed  from  the  Pseudionon  with  steam  distillation.  The  residual 
oil  is  again  fractionated  and  that  fraction  distilling  at  I43°-I45°  (12 
mm)  is  pure  Pseudionon. 
The  products  of  reaction  are  : 
C10HI6O  +  CH3COCH3  =  C13Hi0O  +  H20. 
Pseudionon  is  a  clear,  colorless  oil,  B.  P.  I43°-I45°  (12  mm.); 
sp.  gr.,  0-9044;  index  of  refraction,  nD=i-5275  ;  odor,  characteris- 
tic and  prominent.  Its  phenylhydrazine  and  oxime  compounds  are 
thick  oils.  It  does  not  combine  with  NaHS03.  It  is  changed  by 
alkalies  and  strong  acids  into  resinous  products.  With  dilute  acids,, 
changed  to  Ionon. 
Pseudionon  formula : 
1     2     3     4     5     67     8     9    10  11 
CH./CH-CH.,CH:CHC:CH-CH:CHCO'CH. 
I  I" 
CH,  CH, 
