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This conversion was recently asked in the NSEC, an Indian (preliminary) chemistry olympiad for high schoolers and the official answer key stated LiAlH4 is the correct reagent to be used. However I have come across LAH reducing double bonds conjugated with benzene rings so I thought the double bond would be reduced if it was used. Therefore I assumed the birch reduction would be the appropriate method, but would that reduce the ring itself into some sort of diene? Or is that just for unsubstituted benzene? The other options were the clemmenson (which would kill the carbonyl) and H2/Pd-C (which should kill the double bond)



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