Synthesis of Adamantane

Structure of Adamantane

C10H16

Principal investigatorHermann Stetter
Publication year1956
Synthesis typeTotal
Number of steps 9 (linear)
References
Chem. Ber. 1956, 89, 1922. Chem. Ber. 1955, 88, 1535. Ber. dtsch. Chem. Ges. A/B 1937, 70, 314.
Part 1 of 1
intermediate structure
NaOMe, CH2Br2
120 °C, 10 h, 31 %
"See: Chem. Ber. 1937, 70, 314."
intermediate structure
PtO2, H2
Dioxane
80 °C, 85 %
intermediate structure
HCl, AcOH
H2O
Reflux, 8 h, 85 %
intermediate structure
  1. PCl5
  2. MeOH
120-130 °C, 5 h, 83%
intermediate structure
HCl, AcOH
H2O
Reflux, 12 h, 82 %
intermediate structure
Ni (Raney), NaOH, H2
H2O
50-60 °C, 16 h, 95 %
intermediate structure
NaOH, AgNO3
H2O
intermediate structure
Br2
CCl4
RT to Reflux, 28 h, 70 %
See the Hunsdiecker Reaction
intermediate structure
NaOEt, H2, Ni (Raney)
EtOH
42 %
intermediate structure
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