12 
and  Carvacrol  Problems.     jA™-  J°ur-  *}™m- 
l     January,  1921. 
The  ethereal  solution  was  allowed  to  evaporate  partially  and  the 
crystals  filtered  at  the  pump  and  dried  as  well  as  possible  in  a  vacuum 
desiccator.  The  analysis  indicates  that  excess  carvacrol  from  the 
mother  liquors  remained  on  the  crystals. 
I.  0.7340  Gm.  gave  0.2303  Gm.  Na2S04- 
II.  0.6685   Gm.  gave  0.2070  Gm.  Na2SO.±. 
Sodium  calc.  for  CioHisONa.  Found. 
Per  cent.  Per  cent. 
13.36  I.  10.16 
II.  10.03 
The  crystals  were  dissolved  in  ether  and  this  solution  diluted 
with  benzene  and  the  ether  allowed  to  evaporate.  The  sodium 
compounds  slowly  turns  greenish  in  the  air.  It  dissolves  in  ether 
with  absorption  of  heat.  With  loss  of  ether  fine,  colorless  prisms 
appeared  and  were  filtered  at  the  pump;  washed  with  benzene  to 
remove  excess  of  carvacrol  and.  dried  in  a  vacuum. 
The  melting  point  of  these  crystals  was  72-73 0  and  decomposi- 
tion took  place  very  readily.  For  analysis  it  was  dried  at  500  for 
five  hours  when  a  brownish  color  had  begun  to  develop. 
I.  0.5668  Gm.  lost  0.060    Gm.  and  gave  0.2016  Gm.  Na2SOi. 
II.  0.7395  Gm.  lost  0.0814  Gm.  and  gave  0.2635  Gm.  Na2S04- 
III.  0.6549  Gm.  lost  0.0626  Gm. 
Loss  on  drying:        I.  9.57  p.  c. 
II.  9.92  p.  c. 
iii.  9-56  p.  c.  j 
Sodium    I.  it. 51  p.  c.  on  dried  basis  12.75  p.  c.  calc.  13.36  p.  c. 
II.  11.54  P-  c.  on  dried  basis  12.79  p.  c. 
These  results  correspond  to  the  formula  C10H13ONa  as  the 
composition  of  the  compound  obtained  from  ether. 
Thymol  reacts  with  sodium  in  ether  in  a  lively  manner  but 
nothing  could  be  crystallized  out.  Metallic  sodium  remained 
bright  in  the  solution  which  was  clear  and  almost  colorless.  It 
began  to  oxidize  on  long  standing. 
Carvacrol  is  completely  extracted  from  alkaline  solution  by 
repeatedly  shaking  with  ether.  The  ether  was  evaporated  on  the 
waterbath  and  in  this  way  water  was  retained  by  the  carvacrol. 
This  material  was  obtained  by  working  up  a  Monarda  oil  with  5 
per  cent,  sodium  hydroxide.  To  ascertain  the  amount  of  sodium 
in  the  carvacrol,  presumably  extracted  as  carvacrolate,  a  quantity 
of  the  clear  phenol  was  evaporated  and  the  residue  ignited  in  a 
