Camphor → Bornylene

HRID 4925

Reaction equation

HRID 4925 reaction equation
[CH3:1][C:2]12[C:8]([CH3:10])([CH3:9])[CH:5]([CH2:6][CH2:7]1)[CH2:4][C:3]2=O.C[Li]>CCOCC>[CH3:1][C:2]12[C:8]([CH3:10])([CH3:9])[CH:5]([CH2:6][CH2:7]1)[CH:4]=[CH:3]2

Participants

4

Reactant 2

HCID 2537CamphorHCID 178418348HCID 178418348, compound

Product 1

HCID 10047Bornylene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one (1-camphor) was converted into its 4-toluenesulfonylhydrazone, which was then reacted with methyllithium in ether, to give the title compound. The method used was that described by Shapiro and Duncan, Organic Synthesis, Vol 51, pp 67-69, for the conversion of racemic camphor into racemic 1,7,7-trimethylbicyclo[2.2.1]hept-2-ene.

Sources & evidence

ORD record
ord-58c68fbf10174a44867b9854715d2022
Source dataset
uspto-grants-1993_09
Patent number
US05242911

Linked notes

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