I24 
Urethanes  of  Thymol  and  Carvacrol. 
The  Dumas  method  gave  results  very  close  to  these  on  material 
dried  at  1300  for  one  hour. 
A  methoxyl  determination  gave  no  turbity  in  the  silver  nitrate 
solution  after  four  hours ;  so  there  cannot  be  methoxyl  groups  pres- 
ent. This  percentage  of  nitrogen  does  not  correspond  with  any  pos- 
sible arrangement  of  the  nuclei,  because  the  isocyanate  itself  has- 
only  11.77  per  cent,  nitrogen. 
The  reaction  by  which  this  formed  is  the  ordinary  Schotten- 
Baumann  reaction  in  which  the  phenol  was  dissolved  in  the  theoreti- 
cal quantity  of  15  per  cent,  sodium  hydroxide  and  a  sufficient  quan- 
tity of  benzoyl  chloride  added  to  leave  an  odor  at  the  end. 
Five  grams  of  hydrothymoquinone  (3  mols)  were  dissolved  irt 
a  slight  excess  (20  cc.)  of  15  per  cent,  sodium  hydroxide.  To  the 
brownish  solution  8.4  g.  of  benzoyl  chloride  (6  mols)  were  added 
and  the  mixture  shaken.  Heat  was  evolved  and  a  pale  yellowr 
crystalline  solid  separated.  The  filtrate  yielded  some  benzoic  acid 
on  acidification,  but  this  may  have  been  derived  from  the  excess  of 
alkali.  The  moist  solid  was  washed  at  the  pump  and  treated  with 
about  40  cc.  of  95  per  cent,  alcohol  and  boiled.  A  solution  resulted, 
orange-yellow  in  color,  which  deposited  crystals  on  cooling.  These 
were  taken  up  in  alcohol  and  the  undissolved  portion  from  the  first 
treatment  also  dissolved  in  this  solution. 
The  crystals  appeared  as  coarse  needles,  very  slightly  yellowish 
or  as  a  finely  granular  white  powder. 
I.  0.1432  g.  gave  19.6  cc  N,  at  220  and  705  mm. 
Found 
Nitrogen  14.8  p.  c. 
DIBENZOYL  HYDROTHYMOQUINONE 
From  dilute  alcohol  (ist)  1.16  g.  mp.  138-140°. 
From  95  p.  c.i  alcohol  (2nd)  4.74  g-  mp.  141-1420. 
From  95  p.  c.  alcohol  (3rd)  2.59  g.  mp.  141-1420. 
Yield 
8-49  g-' 
On  the  basis  of  the  dibenzoate,  C10H12(OCOC6H5)2,  this  rep- 
resents a  75.5  per  cent,  yield,  as  computed  only  on  that  recovered 
from  the  alcohol  by  crystallization.    On  analysis : 
