Am.  Jour.  Pharm.) 
April,  1920 J 
Benzyl  Benzoate. 
253 
distilled  from  coal  tar.  These  crude  phenols,  necessarily  dissolved 
in  alkali  to  separate  them  from  the  neutral  oils,  can,  at  that  point, 
by  suitable  means,  be  freed  completely  from  their  impurities,  and 
after  fractional  removal  of  the  phenol  proper,  the  cresols  could  then 
be  recovered  in  pure  form  with  one  operation. 
The  production  of  purified  cresols  is,  therefore,  a  logical  open- 
ing for  American  enterprise,  as  well  as  American  resources,  for  here, 
as  in  Europe,  are  immense  supplies  of  coal  tar  on  which  to  draw  for 
crude  materials. 
BENZYL  BENZOATE.* 
As  the  drug  has  come  into  fairly  extensive  use,  some  notes  on 
its  pharmacy,  chemistry,  and  general  properties  may  be  of  service. 
Benzyl  benzoate,  C6H5COO.C6H5CH2,  is  the  benzyl  alcohol  ester 
of  benzoic  acid.  It  occurs  naturally  in  several  of  the  balsamic 
resins,  such  as  balsam  of  Peru  and  in  balsam  of  tolu.  Possibly  the 
antispasmodic  action  of  these  drugs  is  due  in  some  measure  to  its 
presence.  It  is  contained  in  the  volatile  oils  of  many  fragrant 
flowers,  such  as  hyacinth,  jasmin,  orange,  etc.  It  may  be  obtained 
by  the  fractional  distillation  of  the  oily  portion  of  balsam  of  Peru; 
it  is  made  synthetically  in  several  ways.  On  a  manufacturing  scale 
it  may  be  prepared  either  by  treatment  of  benzyl  chloride  and  ben- 
zoic acid  with  phosphorus  oxychloride,  or  by  treatment  of  benzyl 
chloride  and  sodium  benzoate  with  soda  ash. 
It  is  a  colorless  oily  liquid,  odorless  or  with  a  faint  aromatic  odor, 
and  having  a  sharp  burning  taste.  It  is  insoluble  in  water  or  glycerin,, 
but  is  miscible  in  all  proportions  with  alcohol,  chloroform,  or  ether. 
When  ignited  it  burns  with  a  smoky  flame.  Sp.  Gr.  1.09  to  1.13  at 
15  °  C.  It  is  neutral  to  litmus.  Alcoholic  solution  of  KOH  saponifies 
it  readily.  This  solution  when  neutralized  gives  with  ferric  chloride 
a  flesh-colored  precipitate,  and  upon  acidulation  a  white,  crystalline 
precipitate  of  benzoic  acid  separates.  This  may  be  extracted  with 
ether  and  identified  by  means  of  the  usual  tests  for  benozic  acid. 
Benzyl  benzoate  for  medicinal  purposes  should  be  free  from  chlorine 
and  should  contain  not  less  than  95  per  cent,  of  pure  benzyl  benzoate. 
The  residue  from  ignition  of  10  Cc.  should  weigh  not  more  than 
0.1  Mgm.,  that  is,  practically  nil.  The  volumetric  test  given  by  the 
American  Medical  Association  is  as  follows :  To  about  2  Gms.  benzyl 
*From  The  Prescriher,  March,  1920. 
