32 
Artificial  Musk. 
i  Am.  Jour.  Pharm. 
I       Jan.,  1892. 
quantity  of  the  dinitro-compound.  A  separation  of  the  dinitrobutyl- 
toluene  can  be  more  easily  effected  by  crystallizing  out  the  greater 
part  of  the  trinitrobutyltoluene,  repeatedly  distilling  the  oil  in  a. 
vacuum,  and  collecting  the  fraction  boiling  at  224-225  °.  Dinitro- 
butyltoluene  is  a  brown  oil  of  very  unpleasant  odor,  and  does  not 
solidify  in  a  freezing  mixture.  On  further  nitration,  it  is  converted 
into  artificial  musk. 
Trinitrobutyltoluene  (artificial  musk),  CMe3-C6HMe(N02)3,  is  ob- 
tained when  tertiary  butyltoluene  is  slowly  added  in  the  cold  to  five 
times  its  weight  of  a  mixture  of  I  part  of  nitric  acid  (sp.  gr.  =  1-5), 
and  2  parts  of  1 5  per  cent,  anhydrosulphuric  acid,  and  the  mixture 
afterwards  heated  for  8-9  hours  on  a  water-bath.  It  crystallizes 
from  alcohol  in  yellowish-white  needles,  melts  at  96-970,  is  only 
very  slightly  volatile  with  steam,  and  has  a  powerful  odor  of  musk. 
It  is  insoluble  in  water,  but  it  dissolves  readily  in  alcohol,  ether., 
benzene,  chloroform,  and  light  petroleum.  With  naphthalene  in 
alcoholic  solution,  it  forms  a  compound  2CuH]3(NO2)3C10Hs,  which 
crystallizes  in  large,  yellowish  scales,  melts  at  89-900,  and  decom- 
poses  into  its  generators  on  warming  with  water.  Trinitrobutyl- 
toluene is  not  affected  by  treatment  with  alkalis  or  ammonia,  and 
when  warmed  with  an  excess  of  aniline  forms  a  compound  3CnHia 
(N02)32NH2Ph,  which  crystallizes  from  the  excess  of  aniline  in  com- 
pact forms,  and  melts  at  640.  Of  the  four  possible  formulae  for  a 
trinitrometabutyltoluene,  the  author,  on  these  grounds,  excludes 
the  three  containing  two  nitro-radicles  relatively  in  the  ortho-posi- 
tion, and  assigns  to  artificial  musk  the  remaining  formula  [Me  :  CMe3 
:(N02)3=i:3:2:4:6]. 
Amidobutyltoluene,  CMe3-C6H3Me>NH2,  is  formed  by  the  reduc- 
tion of  nitrobutyltoluene  with  tin  and  hydrochloric  acid.  It  is  a  color- 
less oil,  of  pleasant,  cumin-like  odor,  and  boils  at  2450.  The  acetyl 
derivative,  CnH15-NHAc,  crystallizes  from  alcohol  in  lustrous  scales 
melting  at  1620,  and  the  benzoyl  derivative  in  small,  white  needles 
melting  at  167-1680.  It  is  therefore  identical  with  the  amido- 
compound  obtained  by  Effront  in  1884,  by  heating  isobutyl  alcohol 
with  orthotoluidine  hydrochloride  at  280-3000,  and  must  contain 
the  amidogen  in  the  para-position  relatively  to  the  tertiary  butyl 
radicle. 
Amidodinitrobutyltoluene,  CMe3-C6HMe(N02)2-NH2,  is  obtained 
when  trinitrobutyltoluene  in  alcoholic  solution  is  reduced  with  the 
