Synthesis of Cocaine

C17H21NO4
Principal investigator | Richard Willstätter |
---|---|
Publication year | 1901 |
Synthesis type | Total |
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

CaO
>180 °C, 32%

Na
EtOH
Reflux

HI
H2O
RT to 100 °C, 3 h

KOH
EtOH
Reflux, 83% (3 steps)

Br2
CHCl3
0 °C, 100%

Me2NH
PhH
140 °C, 5 h, 75%

MeI
Acetone
RT


Br2
CHCl3
-5 °C, 82%

Quinoline
150-165 °C, 94%

HBr
AcOH
0 °C to RT, 2 h, 65%

Me2NH
PhH
RT, 24 h, 92%

Na
EtOH
Reflux, 82%

- Br2 , HBr
- Na2CO3
AcOH, H2O

EtOH
Reflux, 30% (2 steps)

- NaOH
- KI
H2O
Reflux, 2 h

AgCl

130 °C, 54% (3 steps)

HBr
AcOH
100 °C, 80 h, 85%

H2SO4
H2O
205-215 °C, 4 h, 24%

CrO3
AcOH, H2O
60-70 °C, 4 h, 80%

Na,
CO2
Et2O
RT to reflux, 2 h, 82%

HCl,
Na(Hg)
H2O
10-12%


Bz2O
PhH
Reflux
"No yield reported."
