Am.  Jour.  Pharm. 
March,  1921. 
|    Ur ethanes  of  Thymol  and  Carvacrol. 
217 
Carvacrol, 
Thymol, 
Weight 
1-54  gm. 
1.62  gm. 
M.  P. 
1420  with  decomp. 
158.5 0  with  decomp. 
They  were  soluble  in  alkalis  and  ammonia  with  a  brown  color 
and  conducted  themselves  like  the  original  nitrosophenols.  Re- 
crystallized  from  heptane  they  melted  as  follows : 
M.  P.      M.  P.  of  nitrosophenols 
If  conversion  into  the  nitroso  derivative  be  complete,  the  yield 
should  be  1.79;  accordingly  that  gives: 
It,  therefore,  becomes  apparent  that  in  the  presence  of  alkali 
the  benzoyl  group  is  split  off,  regenerating  the  original  nitroso- 
compound : 
The  brownish-red  color  obtained  on  adding  an  excess  of  alkali 
is  apparently  that  of  the  nitrosoalkali  derivative.  Heating  in  the 
water  bath  for  three  hours  is  sufficient  to  complete  this  hydrolysis. 
An  insufficient  amount  of  alkali  might  delay  this  reaction.  The 
filtrates  had  the  odor  of  ethyl  benzoate,  strongly,  but  gave  no  pre- 
cipitate on  addition  of  sulphuric  acid,  and  no  attempt  was  made  to 
isolate  benzoic  acid.  The  pale  yellow  color  of  the  liquors  showed 
just  a  perceptible  darkening  with  sodium  hydroxide,  which  may  be 
attributed  to  the  nitrosocompound  remaining  in  solution. 
Next  the  reaction  was  carried  out  in  heptane  solution,  using 
sodium  bicarbonate  to  liberate  hydroxylamine.  Equivalent  quanti- 
ties were  taken : 
These  substances  were  finely  pulverized  and  mixed  and  10  cc. 
heptane  added  as  a  reaction  medium. 
Over  night  the  appearance  of  both  mixtures  had  changed.  The 
carvacrol  reaction  mixture  contained  fine  needles  reaching  to  the 
surface  of  the  heptane.  On  heating  in  a  water  bath  the  entire  mix- 
ture became  crystalline  and  granular  wih  a  rim  of  crystals  adhering 
Carvacrol, 
Thymol, 
Carvacrol, 
Thymol, 
86.0  p.  c. 
90.5  " 
Benzoyl  derivative, 
Hydroxylamine  hydrochloride, 
Sodium  bicarbonate, 
0.71  gm. 
0.18  gm. 
0.21  gm. 
