THE  AMERICAN 
JOURNAL  OF  PHARMACY. 
OCTOBER,  1889. 
ON  THE  ACTION  OF  ACID  CHLORIDES  ON  PHENOL- 
ETHERS. 
By  Henry  C.  C.  Maisch,  Ph.G.,  Ph.D. 
Some  years  ago  Fried  el  and  Crafts  (Comptes  vendues .  (1877) 
lxxxiv  1392,  1450,  lxxxv  74,  etc.)  described  a  synthetical  reaction 
which  has  since  then  been  employed  in  a  great  number  of  cases.  The 
reaction  is  based  on  the  following  :  a  halogen  derivative  of  the  fatty 
group,  in  which  the  halogen  is  bound  to  a  carbon  atom,  acts  on  ben- 
zol or  its  derivatives,  in  the  presence  of  aUi  minium  chloride,  in  such  a 
manner  that  hydrochloric  acid  is  liberated  and  a  new  body,  either  a 
hydrocarbon,  a  ketone  or  an  acid  derivative  is  formed.  Until  a  few 
years  ago  it  was  thought  that  the  reaction  would  only  take  place  if 
one  of  the  reacting  substances  were  a  hydrocarbon  ;  but  Leuckart  and 
M.  Schmidt  (Ber.,  xviii,  (1885),  p.  2338)  showed  this  not  to  be  the  case 
as  the  hydrochloric  acid  addition  product  of  phenylcyanate  Cl-CO- 
NHC6H5  reacts  with  hydrocarbons  as  well  as  with  phenolethers  in 
presence  of  aluminium  chloride.  Continuing  in  this  line  of  research, 
Gattermann  &  Hess  (Liebig's  Ann.  244,  p.  61),  used  the  chloride  of 
the  simple  carbonic  acid  Cl-CO-NH2  and  obtained  amides.  I  am 
greatly  indebted  to  Prof.  L.  Gattermann  for  suggesting  to  me 
the  investigation  of  the  chlorides  of  the  carbon  acids  in  their  effects 
upon  the  phenolethers. 
These  ethers  were  prepared  according  to  the  general  method  by  the 
action  of  potassium  hydrate  in  alcoholic  solution  on  a  mixture  of 
phenol  and  a  halogen  derivative  of  the  group  to  be  introduced.  With 
the  naphthol  ethers  a  simpler  and  cheaper  method  was  found  to  an- 
swer all  purposes.  The  latter  is  the  action  of  10  parts  concentrated 
sulphuric  acid  on  a  solution  of  25  parts  of  a-  or  /9-  naphthol  in  20  parts 
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