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The one-step Claisen rearrangement using ethyl vinyl ether, N,N-dimethylacetamide dimethyl acetal, or t,riethyl orthoacetate provides a useful method for the preparation of octalin systems with functionalized angular methyl groups from octalols.However, preparation and purification of vinyl ethers followed by thermolysis lead to functionalized methyl groups in both ring systems. The use of decalin as solvent in the thermolysis increases the amount of Claisen product in the hydrindeny1 system. When the temperature is lowered, the rate of rearrangement is decreased and the amount of elimination increased.This method fails with the hydrindenyl ring system.