16  Thymol  and  Carvacrol  Problems.      { AJalZy 
and  added  to  the  solvent.  There  was  a  slight  loss  of  solution  in 
these  manipulations  but  the  diminution  in  volume  with  loss  of 
thymol  from  the  solution  and  the  amount  taken  up  by  the  solvent 
always  exceeded  this  quantity. 
Ether.  Heptane. 
A. 
B. 
A. 
B. 
Cc. 
Cc. 
Cc. 
Cc. 
i  st  Extn. 
. .  5o.o 
50.0 
50.0 
50.0 
..  44-7 
45-0 
49-3 
49-1 
2d  Extn. 
Vol.  of  aqueous  soln 
..  44-0 
44-7 
49.0 
48.9 
Vol.  of  aqueous  layer  . . . 
. .  427 
43.o 
48.5 
48.4 
3d  Extn. 
,  .  42.0 
42.6 
48.3 
48.4 
Vol.  of  aqueous  layer  . . . 
..  41.2 
4i-5 
47-7' 
47-6 
The  various  solvents  employed  were  purified  in  approved 
manners.  The  ether  was  washed  with  dilute  alkali ;  dried  over 
calcium  chloride  and,  after  standing  over  sodium,  distilled  in  a  dry 
apparatus.  The  heptane  was  a  very  pure  sample  previously  purified 
by  hydrogen-bromide  and  had  stood  over  sodium  several  months. 
It  was  used  without  distillation  and  probably  boiled  originally  within 
one  degree.  The  benzene  was  dried  over  sodium  and  distilled.  The 
carbon  tetrachloride  and  di sulphide  both  were  washed  with  dilute 
alkali  and  dried  by  standing  over  calcium  chloride  about  a  week. 
These  commercial  products  were  finally  distilled  to  complete  puri- 
fication. 
The  amount  of  thymol  as  determined  by  acidification  and  ex- 
traction with  ether  and  weighing  after  recovery  of  ether  was  7.459 
Gins,  in  50  Cc.  of  solution.  The  concentration  of  alkali  was  4.188 
per  cent.  According  to  Seidell 10  thymol  is  soluble  in  water  at  22 0 
to  the  extent  of  0.0936  Gm.  per  100  Cc.  and  at  250  of  0.0981  Gm. ; 
while  in  dilute  hydrochloric  acid  such  as  resulted  above  the  solu- 
bility is  less.  Extraction  with  ether  would  remove  that  also.  As  a 
rough  check  on  the  results  of  extraction  except  in  the  case  of  ether, 
the  remaining  alkaline  solution  was  acidified  and  the  thymol  weighed 
after  drying  in  the  air  over  night,  or  until  it  became  fairly  constant. 
10  Seidell,  A.  C.  J.,  48  (1912),  p.  453- 
