Synthesis of Ferruginol

Structure of Ferruginol

C20H30O

Principal investigatorFrederick E. King
Publication year1957
Synthesis typeTotal
Number of steps 8 (linear)
References
J. Chem. Soc. 1957, 573.
Part 1 of 1
intermediate structure + intermediate structure
Na, Fe(NO3)3
NH3
-78 °C, 75%
intermediate structure
Pd(OH)2/CaCO3, H2
1-3 atm
EtOH
RT, 30 min, 97%
intermediate structure
P2O5
Vacuum
20 to 150 °C, 90 min, 70%
See the Bogert-Cook Synthesis
intermediate structure
AlCl3, AcCl
PhNO2
5 °C, 4 d, 23%
See the Friedel-Crafts Acylation
"Purified by crystallization of the semicarbazone."
intermediate structure
MeMgI
Et2O
Reflux, 60 min
See the Grignard Reaction
intermediate structure
Ac2O
Reflux, 60 min, 76% (2 steps)
intermediate structure
PtO2, H2
EtOH
RT, 30 min, 88%
intermediate structure
HBr
AcOH, H2O
Reflux, 14 h, 36%
"Purified by crystallization of the benzoate ester."
intermediate structure
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