Am.  Jour.  Pharm,  1 
August.  1907.  J 
Synthetic  Camphor. 
351 
CH3 
I 
CH,  C  CH., 
I  I 
H3C— C — CH3 
I  I 
CH2  =C(OH)-CH, 
Isoborneol. 
Oxidation 
CH3 
CH9  -C  CH, 
I 
H3C— C— CH, 
CH,  CH  CO 
Camphor. 
The  first  patent  on  synthetic  camphor  known  to  the  author  was 
issued  in  Germany,  April  12,  1892,  to  J.  Bertram,  No.  67,255.  It 
consists  in  converting  camphene  into  isoborneol  acetate  with  a  sul- 
phuric-acetic acid  mixture.  The  isoborneol  acetate  so  obtained  is 
saponified,  the  solid  isoborneol  separated  and  oxidized  by  the  usual 
oxidizing  agents. 
Camphene  can  be  prepared  by  treating  pinene  hydrochloride  with 
alcoholic  potash,  potassium  acetate,  glacial  acetic  acid,  sodium  alco- 
holate,  sodium  benzoate,  and  heating  with  water  under  pressure. 
In  1902  Karl  Stephan  was  granted  two  U.  S.  patents,  Nos.  707,270 
and  707,271  respectively.  According  to  the  former  patent  cam- 
phene is  prepared  by  heating  any  hydrogen  haloid  of  pinene  with 
aliphatic  bases  such  as  piperazin,  piperidin  and  diamylamin,  and  by 
the  latter  patent  the  same  pinene  compounds  are  treated  under 
pressure  and  heat  with  alcoholic  ammonia,  aqueous  ammonia  or 
ammonia  gas. 
The  first  process  protected  by  U.  S.  letters-patent  No.  582,221 
for  the  manufacture  of  synthetic  camphor  was  issued  May  II,  1897. 
The  turpentine  is  converted  into  what  is  termed  by  the  patentee 
"  hydrochlorinated  terpene,"  long  known  as  <4  artificial  camphor," 
the  common  name  for  which  is  bornyl  chloride.  It  was  first  pro- 
duced by  Kindt  in  1803  and  considered  by  him  to  be  camphor.  It 
is  claimed  by  the  patentee  that  in  order  to  successfully  produce 
bornyl  chloride,  it  is  absolutely  necessary  to  work  with  anhydrous 
CH, 
CH, 
I 
-C— 
CH 
Addition  of 
water. 
H3C— C— CH3 
CH,  CH  CH 
Camphene. 
