220  Ur ethanes  of  Thymol  and  Carvacrol     \ Am-  J°ur-  Pharm. 
(     March,  1921. 
behaves  similarly,  must  be  broken  down  to  the  nitrosoderivative  by 
alkali.  It  is  very  interesting  to  note  that  apparently  nitrosothymol 
and  not  nitrosocarvacrol  results  by  this  decomposition. 
THE  ALKYL  ETHERS  OF  THE  NITROSOPHENOLS. 
The  formation  of  alkyl  ethers  from  the  different  metallic  nitro- 
soderivatives  was  undertaken  in  an  attempt  to  differentiate  between 
the  two  possible  types.  Since  the  nitrosophenols  may  exist  in  two 
forms  ethers  should  exist  in  two  forms  also  by  replacement  of  the 
hydrogen  by  an  alkyl  radical. 
Bridge  24  obtained  a  methyl  ether  of  nitrosophenol  itself  in  two 
manners.  The  silver  derivative  of  nitrosophenol  and  methyl  iodide 
were  allowed  to  react  in  dry  ether.  By  the  action  of  the  sodium 
derivative  in  methyl  alcohol  on  methyl  iodide  the  same  compound 
was  obtained.  The  yield  was  rather  low  and  much  polymerized 
nitrosophenol  resulted. 
That  the  methyl  group  was  in  the  oxime  and  not  in  the  phenol 
group  was  proven  in  the  case  of  another  derivative,  the  benzoyl 
ether,  which  was  obtained  quantitatively  from  quinone  and  %-benzyl- 
hydroxylamine : 
Goldschmidt  and  Schmid  24a  found  that  the  action  of  methyl 
iodide  on  the  silver  derivative  of  nitrosothymol  gave  only  tars  from 
which  the  original  nitrosocompound  could  be  regenerated.  An  at- 
tempt was  made  to  prepare  the  methyl  derivatives  of  both  phenols 
in  a  similar  manner.  Four  grams  of  the  silver  derivative  were 
mixed  with  the  theoretical  quantity  of  methyl  iodide  and  the  mixture 
warmed  with  a  little  alcohol  under  a  reflux  condenser.  There  re- 
sulted a  brown  solution  and  a  very  pale  residue.  The  carvacrol  re- 
action mixture  was  filtered  and  the  residue  digested  with  dilute  nitric 
acid.  Chlorides  gave  a  copious  precipitate,  showing  that  much  of 
the  silver  compound  remained  undecomposed.  Boiling  with  con- 
centrated nitric  acid  left  practically  no  residue,  showing  that  little 
silver  iodide  had  been  formed  during  the  reaction.  The  thymol 
reaction  mixture  was  steam  distilled,  but  practically  nothing  was 
separated  in  this  manner. 
24  Bridge,  A.  C.«  J.,  14,  p.  276. 
24a  Goldschmidt  and  Schmid,  Ber.,  17  (1884),  P-  2062. 
