Synthesis of Cocaine

Structure of Cocaine

C17H21NO4

Principal investigatorRichard Willstätter
Publication year1901
Synthesis typeTotal
Number of steps 25 (linear)
References
Ber. Dtsch. Chem. Ges. 1901, 34, 1457. Liebigs Ann. 1903, 326, 23. Ber. Dtsch. Chem. Ges. 1901, 34, 129. Ber. Dtsch. Chem. Ges. 1901, 34, 3163. Liebigs Ann. 1901, 317, 204. Liebigs Ann. 1901, 317, 267. Liebigs Ann. 1901, 317, 307. Liebigs Ann. 1903, 326, 42. Ber. Dtsch. Chem. Ges. 1902, 35, 1870. Ber. Dtsch. Chem. Ges. 1896, 29, 393. J. Prakt. Chem. 1894, 49, 409.
Part 1 of 1
intermediate structure
CaO
>180 °C, 32%
intermediate structure
Na
EtOH
Reflux
intermediate structure
HI
H2O
RT to 100 °C, 3 h
intermediate structure
KOH
EtOH
Reflux, 83% (3 steps)
intermediate structure
Br2
CHCl3
0 °C, 100%
intermediate structure
Me2NH
PhH
140 °C, 5 h, 75%
intermediate structure
MeI
Acetone
RT
intermediate structure
Ag2O
H2O
RT to >120 °C, 80%
See the Hofmann Elimination
intermediate structure
Br2
CHCl3
-5 °C, 82%
intermediate structure
Quinoline
150-165 °C, 94%
intermediate structure
HBr
AcOH
0 °C to RT, 2 h, 65%
intermediate structure
Me2NH
PhH
RT, 24 h, 92%
intermediate structure
Na
EtOH
Reflux, 82%
intermediate structure
  1. Br2 , HBr
  2. Na2CO3
AcOH, H2O
intermediate structure
EtOH
Reflux, 30% (2 steps)
intermediate structure
  1. NaOH
  2. KI
H2O
Reflux, 2 h
intermediate structure
AgCl
intermediate structure
130 °C, 54% (3 steps)
intermediate structure
HBr
AcOH
100 °C, 80 h, 85%
intermediate structure
H2SO4
H2O
205-215 °C, 4 h, 24%
intermediate structure
CrO3
AcOH, H2O
60-70 °C, 4 h, 80%
intermediate structure
Na, CO2
Et2O
RT to reflux, 2 h, 82%
intermediate structure
HCl, Na(Hg)
H2O
10-12%
intermediate structure
HCl
MeOH
RT, 1 h
See the Fischer-Speier Esterification
"No yield reported."
intermediate structure
Bz2O
PhH
Reflux
"No yield reported."
intermediate structure
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