Am.  Jour.  Pharm. 
Jan.,  1892. 
Artificial  Musk. 
31 
ARTIFICIAL  MUSK.1 
By  A.  Baur. 
The  artificial  musk  previously  described  (Am.  Jour.  Phar.,  1890, 
489)  was  regarded  as  trinitroisobutyltoluene.  It  is,  however,  a 
derivative,  not  of  isoprimary  but  of  tertiary  butyltoluene,  owing  to 
the  occurrence  in  the  preparation  of  the  hydrocarbon  of  an  intra- 
molecular change,  corresponding  with  that  observed  by  Schramm 
in  the  case  of  the  condensation  of  benzene  with  isobutyl  bromide  by 
the  Friedel-Crafts  method. 
Tertiary  butyltoluene  is  easily  obtained  by  the  action  of  tertiary 
butyl  chloride  on  toluene  in  the  presence  of  aluminium  chloride.  It 
boils  at  185-1870,  and  agrees  in  properties  with  the  so-called  iso- 
butyltoluene.  The  sulphonic  acid,  prepared  by  warming  it  with  con- 
centrated sulphuric  acid,  forms  a  barium  salt  (CnH15S03)2Ba  -j-  H20, 
which  crystallizes  in  white  scales,  and  dissolves  sparingly  in  cold 
water,  but  more  easily  in  hot  water,  and  in  50-60  per  cent,  alcohol. 
The  sulphonamide ,  CHH15-S02NH2,  crystallizes  from  water  in  nacreous 
scales,  and  melts  at  94-95  °.  Earlier  determinations  with  the  sul- 
phonamide prepared  from  so-called  isobutyltoluene  gave  74-75°  as 
the  melting  point,  and  this  value  is  always  obtained  with  the  freshly- 
prepared  substance ;  after  being  kept  for  some  hours,  the  melting 
point  is  found  to  have  risen  to  and  remains  constant  at  94-95 °. 
The  trinitrobutyltoluene  formed  by  the  nitration  of  tertiary  butyl- 
toluene melts  at  96-970,  and  is  identical  with  the  product  from 
so-called  isobutyltoluene. 
Nitrobutyltoluener  CMe3-C6H3Me-N02,  is  obtained  by  slowly  adding 
fuming  nitric  acid  to  a  solution  of  tertiary  butyltoluene  in  acetic  acid. 
It  is  a  yellowish  oil  of  a  peculiar  and  slightly  unpleasant  odor,  boils 
at  160-1620  in  a  vacuum  without  decomposition,  and  is  readily 
volatile  with  steam.  On  treatment  with  excess  of  nitric  acid,  it  is 
converted  into  artificial  musk. 
Dinitrobutyltoluene,  CMe3-C6H2Me(N02)2,  is  formed,  together  with 
the  mononitro-  and  trinitro-derivatives  when  tertiary  butyltoluene  is 
dissolved  in  well-cooled  nitric  acid  of  sp.  gr.  1-5.  On  distillation 
with  steam,  the  mononitro-derivative  passes  over  first,  and  then  a 
mixture  of  the  mononitro-  and  dinitro-derivatives  distils  over,  leav- 
ing a  residue  of  the  trinitro-derivative  mixed  with  a  very  small 
1  Reprinted  from  Jour.  Chem.  Soc,  1891,  1464  {Ber.,  24,  2832-2843). 
