Synthesis of Kekulene

Structure of Kekulene

C48H24

Principal investigator	Heinz A. Staab
Publication year	1978
Synthesis type	Total
Number of steps	14 (2 parts)
References	Angew. Chem. Int. Ed. 1978, 17, 372. Chem. Ber. 1983, 116, 3487.

Part 1 of 2

intermediate structure

HNO3

0 to 100 °C, 9.5 h

intermediate structure

PhCHO, Piperidine

135-140 °C, 12.5 h, 37% (2 steps)

intermediate structure

Pd/C, H2

90 atm

EtOAc, EtOH

RT to 50 °C, 15 h, 62%

intermediate structure

i-AmylONO, Cu, H2SO4

EtOH

RT, 7 h, 12%

See the Pschorr Reaction

intermediate structure

HBr, H3PO4, (CH2O)n

AcOH, H2O

80 to 120 °C, 8.5 h, 51%

See the Blanc Halomethylation

intermediate structure

Thiourea

EtOH

Reflux, 48 h

intermediate structure

KOH

H2O

Reflux, 3 h, 76% (2 steps)

intermediate structure

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Part 2 of 2

intermediate structure

+

intermediate structure

KOH

EtOH, PhH

Reflux, 24 h, 60%

intermediate structure

FSO3Me

CH2Cl2

RT, 6 h, 92%

intermediate structure

KOt-Bu

THF

RT, 12 h, 75%

See the Stevens Rearrangement

intermediate structure

mCPBA

CH2Cl2

-20 °C, 10 min, 95%

intermediate structure

450 °C, 30 min, 43%

intermediate structure

I2

hv

PhH

RT, 10 min, 70%

intermediate structure

DDQ

1,2,4-Trichlorobenzene

100 °C, 3 d, 91%

intermediate structure

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