Synthesis of Kekulene

C48H24
Principal investigator | Heinz A. Staab |
---|---|
Publication year | 1978 |
Synthesis type | Total |
Number of steps | 14 (2 parts) |
References |
Part 1 of 2

HNO3
0 to 100 °C, 9.5 h

PhCHO,
Piperidine
135-140 °C, 12.5 h, 37% (2 steps)

Pd/C,
H2
90 atm
EtOAc, EtOH
RT to 50 °C, 15 h, 62%



Thiourea
EtOH
Reflux, 48 h

KOH
H2O
Reflux, 3 h, 76% (2 steps)

Part 2 of 2
+


KOH
EtOH, PhH
Reflux, 24 h, 60%

FSO3Me
CH2Cl2
RT, 6 h, 92%


mCPBA
CH2Cl2
-20 °C, 10 min, 95%

450 °C, 30 min, 43%

I2
hv
PhH
RT, 10 min, 70%

DDQ
1,2,4-Trichlorobenzene
100 °C, 3 d, 91%
