218  Ur ethanes  of  Thymol  and  Carvacrol.    {Al^^'  §2i.rm' 
to  the  flask.  The  thymol  reaction  mixture  formed  a  mush  of  crys- 
tals that  fluffed  up  and  filled  the  liquid  completely.  Both  mixtures 
were  extracted  repeatedly  with  heptane  and  allowed  to  crystallize 
after  each  extraction.  The  carvacrol  mixture  gave  finely  granular 
yellow  crystals ;  while  the  thymol  mixture  gave  a  gelatinous  precipi- 
tate which  filtered  with  difficulty  and  dried  to  a  pale  yellow  film. 
M.  P. 
Carvacrol,  ist  crop  1290 
3rd  crop      134-135 0  no  evolution  of  gas. 
Thymol,  146-147 0  with  decomp. 
The  heptane  solution  of  carvacrol  gave  a  few  crystals  on  evapo- 
ration which  gradually  acquired  a  bright  red  color  and  a  peppery 
odor.  That  of  the  thymol  evaporated  leaving  a  pale  cream  colored 
amorphous  film  which  did  not  become  discolored.  It  had  a  very 
faint  peppery  odor.  The  amount  of  each  recovered  by  crystalliza- 
tion from  heptane  represented  a  yield  of  68  per  cent,  for  carvacrol 
and  62  per  cent,  for  thymol. 
These  substances  dissolve  in  alcohol  with  a  reddish  to  yellowish 
color  and  on  addition  of  water  become  turbid,  and  finally  deposit 
crystals.  Those  for  carvacrol  are  very  long  hairlike,  those  for 
thymol  short  glistening  prisms.  The  quantity  was  too  small  to  work 
with,  but  melting  points  were  determined. 
Carvacrol  Thymol 
ist  sample,  Soft  1640  163-165 0  decompj 
2nd  sample,  1520  165-1660  165-1660 
Oxime  in  parallel,         1280  1320  146-1490 
These  may  be  the  original  nitrosocompounds,  but-  they  appear 
to  be  the  same  substance. 
Alkalis  give  an  immediate  red-brown  color,  showing  decom- 
position, but  a  precipitate  remains  even  after  boiling.  The  possi- 
bility of  formation  of  the  dioxime  above  is  considered,  but  this 
should  be  soluble  in  alkali,  and  melts  after  crystallization  from  alco- 
hol, at  2550  with  decomposition.  This  apparently  rules  out  the 
product  melting  at  165  °.  It  may  be  that  hydrolysis  takes  place  in 
such  a  manner  that  each  gives  the  same  isomeric  form,  namely, 
nitrosothymol. 
Further  quantities  of  the  oximes  were  prepared,  using  5.56  g. 
benzoyl  derivative  in  50  cc.  heptane.  Carbon  dioxide  was  given  off 
very  soon,  and  on  standing  in  the  cold  pressure  developed  continu- 
